WO2019009052A1 - Polycyclic aromatic compound - Google Patents
Polycyclic aromatic compound Download PDFInfo
- Publication number
- WO2019009052A1 WO2019009052A1 PCT/JP2018/023072 JP2018023072W WO2019009052A1 WO 2019009052 A1 WO2019009052 A1 WO 2019009052A1 JP 2018023072 W JP2018023072 W JP 2018023072W WO 2019009052 A1 WO2019009052 A1 WO 2019009052A1
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- WO
- WIPO (PCT)
- Prior art keywords
- formula
- ring
- aryl
- alkyl
- substituted
- Prior art date
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- -1 Polycyclic aromatic compound Chemical class 0.000 title claims abstract description 356
- 125000003118 aryl group Chemical group 0.000 claims abstract description 277
- 239000000463 material Substances 0.000 claims abstract description 139
- 150000001875 compounds Chemical group 0.000 claims description 333
- 125000000217 alkyl group Chemical group 0.000 claims description 230
- 125000004432 carbon atom Chemical group C* 0.000 claims description 174
- 125000001072 heteroaryl group Chemical group 0.000 claims description 137
- 229910052739 hydrogen Inorganic materials 0.000 claims description 107
- 239000001257 hydrogen Substances 0.000 claims description 107
- 238000002347 injection Methods 0.000 claims description 65
- 239000007924 injection Substances 0.000 claims description 65
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 62
- 229910052799 carbon Inorganic materials 0.000 claims description 36
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 35
- 229910052751 metal Inorganic materials 0.000 claims description 31
- 239000002184 metal Substances 0.000 claims description 31
- YZCKVEUIGOORGS-OUBTZVSYSA-N Deuterium Chemical group [2H] YZCKVEUIGOORGS-OUBTZVSYSA-N 0.000 claims description 25
- 229910052805 deuterium Inorganic materials 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 23
- 150000002367 halogens Chemical group 0.000 claims description 23
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 21
- 125000003107 substituted aryl group Chemical group 0.000 claims description 18
- 239000010409 thin film Substances 0.000 claims description 18
- 229910052783 alkali metal Inorganic materials 0.000 claims description 16
- 150000001340 alkali metals Chemical class 0.000 claims description 16
- HKMTVMBEALTRRR-UHFFFAOYSA-N Benzo[a]fluorene Chemical class C1=CC=CC2=C3CC4=CC=CC=C4C3=CC=C21 HKMTVMBEALTRRR-UHFFFAOYSA-N 0.000 claims description 14
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 claims description 13
- 150000004820 halides Chemical class 0.000 claims description 13
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 13
- 150000002910 rare earth metals Chemical class 0.000 claims description 13
- 229910052784 alkaline earth metal Inorganic materials 0.000 claims description 12
- 150000001342 alkaline earth metals Chemical class 0.000 claims description 12
- 125000005647 linker group Chemical group 0.000 claims description 12
- UORVGPXVDQYIDP-BJUDXGSMSA-N borane Chemical group [10BH3] UORVGPXVDQYIDP-BJUDXGSMSA-N 0.000 claims description 11
- 125000003003 spiro group Chemical group 0.000 claims description 11
- 150000001454 anthracenes Chemical class 0.000 claims description 10
- 230000005669 field effect Effects 0.000 claims description 9
- 229920000642 polymer Polymers 0.000 claims description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 7
- MPQXHAGKBWFSNV-UHFFFAOYSA-N oxidophosphanium Chemical class [PH3]=O MPQXHAGKBWFSNV-UHFFFAOYSA-N 0.000 claims description 7
- 150000003222 pyridines Chemical class 0.000 claims description 7
- LISFMEBWQUVKPJ-UHFFFAOYSA-N quinolin-2-ol Chemical compound C1=CC=C2NC(=O)C=CC2=C1 LISFMEBWQUVKPJ-UHFFFAOYSA-N 0.000 claims description 7
- 150000003918 triazines Chemical class 0.000 claims description 7
- 150000003230 pyrimidines Chemical class 0.000 claims description 6
- 150000002219 fluoranthenes Chemical class 0.000 claims description 5
- 150000005041 phenanthrolines Chemical class 0.000 claims description 4
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 229940058303 antinematodal benzimidazole derivative Drugs 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 6
- 150000001716 carbazoles Chemical class 0.000 claims 1
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 abstract description 52
- 229910052796 boron Inorganic materials 0.000 abstract description 18
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 abstract description 16
- 229910052717 sulfur Inorganic materials 0.000 abstract description 11
- 229910052760 oxygen Inorganic materials 0.000 abstract description 9
- 239000001301 oxygen Substances 0.000 abstract description 9
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 abstract description 8
- 239000011593 sulfur Substances 0.000 abstract description 8
- BUGBHKTXTAQXES-UHFFFAOYSA-N Selenium Chemical group [Se] BUGBHKTXTAQXES-UHFFFAOYSA-N 0.000 abstract description 2
- 229910052711 selenium Inorganic materials 0.000 abstract description 2
- MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 abstract 1
- 239000010410 layer Substances 0.000 description 245
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 189
- 230000015572 biosynthetic process Effects 0.000 description 123
- 238000003786 synthesis reaction Methods 0.000 description 122
- 239000007787 solid Substances 0.000 description 98
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 90
- 125000001424 substituent group Chemical group 0.000 description 84
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 73
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 70
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 69
- 238000006243 chemical reaction Methods 0.000 description 64
- 229910052757 nitrogen Chemical group 0.000 description 60
- 239000000543 intermediate Substances 0.000 description 56
- 239000012044 organic layer Substances 0.000 description 56
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 54
- 239000000758 substrate Substances 0.000 description 52
- 230000032258 transport Effects 0.000 description 51
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 49
- 229910002027 silica gel Inorganic materials 0.000 description 49
- 239000000741 silica gel Substances 0.000 description 49
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 48
- 238000005401 electroluminescence Methods 0.000 description 46
- 239000000243 solution Substances 0.000 description 44
- 238000000034 method Methods 0.000 description 43
- 238000005160 1H NMR spectroscopy Methods 0.000 description 42
- 238000005481 NMR spectroscopy Methods 0.000 description 42
- 239000010408 film Substances 0.000 description 41
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 38
- 125000003545 alkoxy group Chemical group 0.000 description 34
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 34
- 125000000753 cycloalkyl group Chemical group 0.000 description 31
- 125000001624 naphthyl group Chemical group 0.000 description 30
- 239000011541 reaction mixture Substances 0.000 description 30
- 239000012299 nitrogen atmosphere Substances 0.000 description 29
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 28
- 229910052782 aluminium Inorganic materials 0.000 description 28
- ILAHWRKJUDSMFH-UHFFFAOYSA-N boron tribromide Chemical compound BrB(Br)Br ILAHWRKJUDSMFH-UHFFFAOYSA-N 0.000 description 28
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 27
- 230000005525 hole transport Effects 0.000 description 27
- 239000002019 doping agent Substances 0.000 description 26
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 26
- 238000003756 stirring Methods 0.000 description 25
- MZRVEZGGRBJDDB-UHFFFAOYSA-N N-Butyllithium Chemical compound [Li]CCCC MZRVEZGGRBJDDB-UHFFFAOYSA-N 0.000 description 24
- 239000002994 raw material Substances 0.000 description 24
- YTZKOQUCBOVLHL-UHFFFAOYSA-N tert-butylbenzene Chemical compound CC(C)(C)C1=CC=CC=C1 YTZKOQUCBOVLHL-UHFFFAOYSA-N 0.000 description 24
- 125000000609 carbazolyl group Chemical class C1(=CC=CC=2C3=CC=CC=C3NC12)* 0.000 description 23
- 239000003480 eluent Substances 0.000 description 23
- 125000003983 fluorenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3CC12)* 0.000 description 23
- 239000000203 mixture Substances 0.000 description 23
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 23
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 22
- PQXKHYXIUOZZFA-UHFFFAOYSA-M lithium fluoride Chemical compound [Li+].[F-] PQXKHYXIUOZZFA-UHFFFAOYSA-M 0.000 description 22
- 239000000126 substance Substances 0.000 description 22
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 22
- 238000010992 reflux Methods 0.000 description 21
- 239000002904 solvent Substances 0.000 description 21
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 20
- 238000000151 deposition Methods 0.000 description 20
- 230000008021 deposition Effects 0.000 description 20
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 20
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 19
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 18
- 125000004986 diarylamino group Chemical group 0.000 description 18
- 125000004104 aryloxy group Chemical group 0.000 description 17
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical group C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 17
- 229910000027 potassium carbonate Inorganic materials 0.000 description 17
- 239000008096 xylene Substances 0.000 description 16
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 15
- 239000012043 crude product Substances 0.000 description 15
- 239000011521 glass Substances 0.000 description 15
- 229910052744 lithium Inorganic materials 0.000 description 15
- 238000004519 manufacturing process Methods 0.000 description 15
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 15
- 125000001828 phenalenyl group Chemical group C1(C=CC2=CC=CC3=CC=CC1=C23)* 0.000 description 15
- 239000007858 starting material Substances 0.000 description 15
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 14
- UBJFKNSINUCEAL-UHFFFAOYSA-N lithium;2-methylpropane Chemical compound [Li+].C[C-](C)C UBJFKNSINUCEAL-UHFFFAOYSA-N 0.000 description 14
- LWIHDJKSTIGBAC-UHFFFAOYSA-K tripotassium phosphate Chemical compound [K+].[K+].[K+].[O-]P([O-])([O-])=O LWIHDJKSTIGBAC-UHFFFAOYSA-K 0.000 description 14
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 13
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 13
- SKTCDJAMAYNROS-UHFFFAOYSA-N methoxycyclopentane Chemical compound COC1CCCC1 SKTCDJAMAYNROS-UHFFFAOYSA-N 0.000 description 13
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical group C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 13
- 239000004065 semiconductor Substances 0.000 description 13
- MFRIHAYPQRLWNB-UHFFFAOYSA-N sodium tert-butoxide Chemical compound [Na+].CC(C)(C)[O-] MFRIHAYPQRLWNB-UHFFFAOYSA-N 0.000 description 13
- 238000010189 synthetic method Methods 0.000 description 13
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 12
- ZADPBFCGQRWHPN-UHFFFAOYSA-N boronic acid Chemical compound OBO ZADPBFCGQRWHPN-UHFFFAOYSA-N 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 12
- 125000005240 diheteroarylamino group Chemical group 0.000 description 12
- 239000000706 filtrate Substances 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 12
- 125000001181 organosilyl group Chemical group [SiH3]* 0.000 description 12
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 12
- 125000004429 atom Chemical group 0.000 description 11
- 239000000460 chlorine Substances 0.000 description 11
- 238000001816 cooling Methods 0.000 description 11
- 125000000623 heterocyclic group Chemical group 0.000 description 11
- 239000003921 oil Substances 0.000 description 11
- 125000005561 phenanthryl group Chemical group 0.000 description 11
- 125000001622 2-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C(*)C([H])=C([H])C2=C1[H] 0.000 description 10
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 125000005842 heteroatom Chemical group 0.000 description 10
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 10
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 10
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 10
- 125000005580 triphenylene group Chemical group 0.000 description 10
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 9
- MRWWWZLJWNIEEJ-UHFFFAOYSA-N 4,4,5,5-tetramethyl-2-propan-2-yloxy-1,3,2-dioxaborolane Chemical compound CC(C)OB1OC(C)(C)C(C)(C)O1 MRWWWZLJWNIEEJ-UHFFFAOYSA-N 0.000 description 9
- UJOBWOGCFQCDNV-UHFFFAOYSA-N 9H-carbazole Chemical compound C1=CC=C2C3=CC=CC=C3NC2=C1 UJOBWOGCFQCDNV-UHFFFAOYSA-N 0.000 description 9
- 239000002841 Lewis acid Substances 0.000 description 9
- WTLFKMLAJZPBSQ-UHFFFAOYSA-N O1C2=C3B(C4=C(OC3=CC=C2)C=CC=C4)C2=CC=C(C=C12)Cl Chemical compound O1C2=C3B(C4=C(OC3=CC=C2)C=CC=C4)C2=CC=C(C=C12)Cl WTLFKMLAJZPBSQ-UHFFFAOYSA-N 0.000 description 9
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 9
- 150000001412 amines Chemical class 0.000 description 9
- 125000005577 anthracene group Chemical group 0.000 description 9
- 229910052792 caesium Inorganic materials 0.000 description 9
- 150000004775 coumarins Chemical class 0.000 description 9
- 238000001914 filtration Methods 0.000 description 9
- 150000007517 lewis acids Chemical class 0.000 description 9
- 239000011777 magnesium Substances 0.000 description 9
- 239000011159 matrix material Substances 0.000 description 9
- 125000004076 pyridyl group Chemical group 0.000 description 9
- PJANXHGTPQOBST-UHFFFAOYSA-N stilbene Chemical class C=1C=CC=CC=1C=CC1=CC=CC=C1 PJANXHGTPQOBST-UHFFFAOYSA-N 0.000 description 9
- LDFCHUHQZQRSHF-UHFFFAOYSA-N 9-(4-bromophenyl)-10-phenylanthracene Chemical compound C1=CC(Br)=CC=C1C(C1=CC=CC=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 LDFCHUHQZQRSHF-UHFFFAOYSA-N 0.000 description 8
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 8
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 8
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical group C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 8
- 125000000641 acridinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3C=C12)* 0.000 description 8
- 125000000732 arylene group Chemical group 0.000 description 8
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 8
- 229910052801 chlorine Inorganic materials 0.000 description 8
- WDECIBYCCFPHNR-UHFFFAOYSA-N chrysene Chemical compound C1=CC=CC2=CC=C3C4=CC=CC=C4C=CC3=C21 WDECIBYCCFPHNR-UHFFFAOYSA-N 0.000 description 8
- 238000010438 heat treatment Methods 0.000 description 8
- 125000001041 indolyl group Chemical group 0.000 description 8
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 8
- SCVFZCLFOSHCOH-UHFFFAOYSA-M potassium acetate Chemical compound [K+].CC([O-])=O SCVFZCLFOSHCOH-UHFFFAOYSA-M 0.000 description 8
- 125000001725 pyrenyl group Chemical group 0.000 description 8
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 8
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 8
- 239000001632 sodium acetate Substances 0.000 description 8
- 235000017281 sodium acetate Nutrition 0.000 description 8
- 125000001544 thienyl group Chemical group 0.000 description 8
- 125000001425 triazolyl group Chemical group 0.000 description 8
- RVPCPPWNSMAZKR-UHFFFAOYSA-N (10-phenylanthracen-9-yl)boronic acid Chemical compound C12=CC=CC=C2C(B(O)O)=C2C=CC=CC2=C1C1=CC=CC=C1 RVPCPPWNSMAZKR-UHFFFAOYSA-N 0.000 description 7
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical group C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 7
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 7
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 7
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 7
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 7
- 239000007983 Tris buffer Substances 0.000 description 7
- 238000009835 boiling Methods 0.000 description 7
- 239000003153 chemical reaction reagent Substances 0.000 description 7
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical class C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 7
- 125000002883 imidazolyl group Chemical group 0.000 description 7
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 7
- WGOPGODQLGJZGL-UHFFFAOYSA-N lithium;butane Chemical compound [Li+].CC[CH-]C WGOPGODQLGJZGL-UHFFFAOYSA-N 0.000 description 7
- 229910052749 magnesium Inorganic materials 0.000 description 7
- 150000002739 metals Chemical class 0.000 description 7
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 7
- 125000002971 oxazolyl group Chemical group 0.000 description 7
- YJVFFLUZDVXJQI-UHFFFAOYSA-L palladium(ii) acetate Chemical compound [Pd+2].CC([O-])=O.CC([O-])=O YJVFFLUZDVXJQI-UHFFFAOYSA-L 0.000 description 7
- 125000000168 pyrrolyl group Chemical group 0.000 description 7
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 7
- 229910052709 silver Inorganic materials 0.000 description 7
- 239000004332 silver Substances 0.000 description 7
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 7
- 238000007740 vapor deposition Methods 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical compound C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 6
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- NANUBXRTTQXXDS-UHFFFAOYSA-N 9-bromo-10-(2-phenylphenyl)anthracene Chemical compound C12=CC=CC=C2C(Br)=C2C=CC=CC2=C1C1=CC=CC=C1C1=CC=CC=C1 NANUBXRTTQXXDS-UHFFFAOYSA-N 0.000 description 6
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
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- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
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- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic System
- C07F5/02—Boron compounds
- C07F5/027—Organoboranes and organoborohydrides
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/30—Coordination compounds
- H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
- H10K85/322—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising boron
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- C—CHEMISTRY; METALLURGY
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- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic System
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0803—Compounds with Si-C or Si-Si linkages
- C07F7/081—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te
- C07F7/0812—Compounds with Si-C or Si-Si linkages comprising at least one atom selected from the elements N, O, halogen, S, Se or Te comprising a heterocyclic ring
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
- H01L29/00—Semiconductor devices adapted for rectifying, amplifying, oscillating or switching, or capacitors or resistors with at least one potential-jump barrier or surface barrier, e.g. PN junction depletion layer or carrier concentration layer; Details of semiconductor bodies or of electrodes thereof ; Multistep manufacturing processes therefor
- H01L29/66—Types of semiconductor device ; Multistep manufacturing processes therefor
- H01L29/68—Types of semiconductor device ; Multistep manufacturing processes therefor controllable by only the electric current supplied, or only the electric potential applied, to an electrode which does not carry the current to be rectified, amplified or switched
- H01L29/76—Unipolar devices, e.g. field effect transistors
- H01L29/772—Field effect transistors
- H01L29/78—Field effect transistors with field effect produced by an insulated gate
- H01L29/786—Thin film transistors, i.e. transistors with a channel being at least partly a thin film
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K59/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic light-emitting element covered by group H10K50/00
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- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
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Abstract
Description
下記一般式(1)で表される多環芳香族化合物。
X1およびX2は、それぞれ独立して、>O、>Sまたは>Seであり、
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10およびR11は、それぞれ独立して、水素、アルキル、またはアルキルで置換されていてもよいアリールであり、R1~R11のうちの隣接する基同士が結合してa環、b環またはc環と共にアリール環を形成していてもよく、形成されたアリール環における少なくとも1つの水素はアルキルで置換されていてもよく、
R1~R11のうちの少なくとも1つは、それぞれ独立して、下記式(Z-1)、式(Z-2)、式(Z-3)、式(Z-4)、式(Z-5)または式(Z-6)で表される基であり、
上記式(Z-1)~式(Z-6)中のArは、それぞれ独立して、下記式(Ar-1)、式(Ar-2)、式(Ar-3)、式(Ar-4)、式(Ar-5)、式(Ar-6)、式(Ar-7)、式(Ar-8)、式(Ar-9)、式(Ar-10)、式(Ar-11)または式(Ar-12)で表される基であり、
上記式(Ar-1)~式(Ar-12)中、Xは、それぞれ独立して、水素、炭素数1~4のアルキル、炭素数1~4のアルキルで置換されていてもよい炭素数6~18のアリール、または炭素数1~4のアルキルで置換されていてもよい炭素数2~18のヘテロアリールであり、A1とA2は、共に、水素であるか、または互いに結合してスピロ環を形成してもよく、式(Ar-1)および式(Ar-2)中の「-Xn」は、n個のXがそれぞれ独立して任意の位置に結合することを示し、nは1~4の整数であり、
上記式(1)で表される化合物における少なくとも1つの水素は重水素で置換されていてもよい。)
The polycyclic aromatic compound represented by following General formula (1).
X 1 and X 2 are each independently>O,> S or> Se,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently substituted with hydrogen, alkyl or alkyl And adjacent groups of R 1 to R 11 may combine to form an aryl ring together with the a ring, b ring or c ring, and at least one of the formed aryl rings is Hydrogen may be substituted by alkyl,
At least one of R 1 to R 11 is each independently represented by the following formula (Z-1), formula (Z-2), formula (Z-3), formula (Z-4), or formula (Z) -5) or a group represented by formula (Z-6),
Ar in each of the above formulas (Z-1) to (Z-6) is independently at each of the following formulas (Ar-1), (Ar-2), (Ar-3), and (Ar-). 4) Formula (Ar-5), Formula (Ar-6), Formula (Ar-7), Formula (Ar-8), Formula (Ar-9), Formula (Ar-10), Formula (Ar-11) Or a group represented by formula (Ar-12),
In the above formulas (Ar-1) to (Ar-12), X is each independently hydrogen, alkyl having 1 to 4 carbon atoms, or carbon number which may be substituted with alkyl having 1 to 4 carbon atoms 6 to 18 aryl or C 2 to C 18 heteroaryl which may be substituted with C 1 to C 4 alkyl, and A 1 and A 2 are both hydrogen or they are bonded to each other May form a spiro ring, and “—Xn” in the formula (Ar-1) and the formula (Ar-2) indicates that n Xs independently bind to any position, n is an integer of 1 to 4 and
At least one hydrogen in the compound represented by the above formula (1) may be substituted with deuterium. )
上記式(1)中、
X1およびX2は、それぞれ独立して、>O、>Sまたは>Seであり、
R1~R11は、それぞれ独立して、水素、炭素数1~12のアルキル、または炭素数1~12のアルキルで置換されていてもよい炭素数6~24のアリールであり、R1~R11のうちの隣接する基同士が結合してa環、b環またはc環と共に炭素数10~20のアリール環を形成していてもよく、形成されたアリール環における少なくとも1つの水素は炭素数1~12のアルキルで置換されていてもよく、
R1~R11のうちの1つまたは2つは、それぞれ独立して、上記式(Z-1)、式(Z-2)、式(Z-3)、式(Z-4)、式(Z-5)または式(Z-6)で表される基であり、
上記式(Z-1)~式(Z-6)中のArは、それぞれ独立して、上記式(Ar-1)、式(Ar-2)、式(Ar-3)、式(Ar-4)、式(Ar-5)、式(Ar-6)、式(Ar-7)、式(Ar-8)、式(Ar-9)、式(Ar-10)、式(Ar-11)または式(Ar-12)で表される基であり、
上記式(Ar-1)~式(Ar-12)中、Xは、それぞれ独立して、水素、炭素数1~4のアルキル、炭素数1~4のアルキルで置換されていてもよい炭素数6~18のアリール、または炭素数1~4のアルキルで置換されていてもよい炭素数4~16のヘテロアリールであり、A1とA2は、共に、水素であるか、または互いに結合してスピロ環を形成してもよく、式(Ar-1)および式(Ar-2)中の「-Xn」は、n個のXがそれぞれ独立して任意の位置に結合することを示し、nは1~4の整数であり、
上記式(1)で表される化合物における少なくとも1つの水素は重水素で置換されていてもよい、
項1に記載する、多環芳香族化合物。 Item 2.
In the above formula (1),
X 1 and X 2 are each independently>O,> S or> Se,
R 1 to R 11 are each independently hydrogen, alkyl having 1 to 12 carbons, or aryl having 6 to 24 carbons which may be substituted with alkyl having 1 to 12 carbons, and R 1 to Adjacent groups of R 11 may combine to form an aryl ring having a carbon number of 10 to 20 together with the a ring, b ring or c ring, and at least one hydrogen in the formed aryl ring is carbon It may be substituted by the alkyl of the number 1-12,
One or two of R 1 to R 11 are each independently the above-mentioned formula (Z-1), formula (Z-2), formula (Z-3), formula (Z-4), formula A group represented by (Z-5) or formula (Z-6),
Ar in the above formulas (Z-1) to (Z-6) is independently at least one of the above formulas (Ar-1), (Ar-2), (Ar-3), and (Ar-). 4) Formula (Ar-5), Formula (Ar-6), Formula (Ar-7), Formula (Ar-8), Formula (Ar-9), Formula (Ar-10), Formula (Ar-11) Or a group represented by formula (Ar-12),
In the above formulas (Ar-1) to (Ar-12), X is each independently hydrogen, alkyl having 1 to 4 carbon atoms, or carbon number which may be substituted with alkyl having 1 to 4 carbon atoms 6 to 18 aryl or
At least one hydrogen in the compound represented by the above formula (1) may be substituted with deuterium.
The polycyclic aromatic compound described in
上記式(1)中、
X1およびX2は、>Oであり、
R1~R11は、それぞれ独立して、水素、炭素数1~6のアルキル、または炭素数1~6のアルキルで置換されていてもよい炭素数6~18のアリールであり、R1~R11のうちの隣接する基同士が結合してa環、b環またはc環と共に炭素数10~18のアリール環を形成していてもよく、形成されたアリール環における少なくとも1つの水素は炭素数1~6のアルキルで置換されていてもよく、
R1~R11のうちの1つまたは2つは、それぞれ独立して、上記式(Z-1)、式(Z-2)、式(Z-3)、式(Z-4)、式(Z-5)または式(Z-6)で表される基であり、
上記式(Z-1)~式(Z-6)中のArは、それぞれ独立して、下記式(Ar-1-1)、式(Ar-1-2)、式(Ar-2-1)、式(Ar-2-2)、式(Ar-2-3)、式(Ar-3)、式(Ar-4-1)、式(Ar-5-1)、式(Ar-5-2)、式(Ar-5-3)、式(Ar-6)、式(Ar-7)、式(Ar-8)、式(Ar-9)、式(Ar-10)、式(Ar-11)または式(Ar-12)で表される基であり、
項1に記載する、多環芳香族化合物。 Item 3.
In the above formula (1),
X 1 and X 2 are> O,
R 1 - R 11 are each independently hydrogen, alkyl having 1 to 6 carbon atoms or an alkyl aryl of 6-18 carbon atoms which may be substituted having 1 to 6 carbon atoms,, R 1 - Adjacent groups of R 11 may combine to form an aryl ring having a carbon number of 10 to 18 together with the a ring, b ring or c ring, and at least one hydrogen in the formed aryl ring is carbon It may be substituted with alkyl of 1 to 6,
One or two of R 1 to R 11 are each independently the above-mentioned formula (Z-1), formula (Z-2), formula (Z-3), formula (Z-4), formula A group represented by (Z-5) or formula (Z-6),
Ar in the above formulas (Z-1) to (Z-6) is independently at least one of the following formulas (Ar-1-1), (Ar-1-2), and (Ar-2-1). ), Formula (Ar-2-2), formula (Ar-2-3), formula (Ar-3), formula (Ar-4-1), formula (Ar-5-1), formula (Ar-5) -2), formula (Ar-5-3), formula (Ar-6), formula (Ar-7), formula (Ar-8), formula (Ar-9), formula (Ar-10), formula ( Ar-11) or a group represented by formula (Ar-12),
The polycyclic aromatic compound described in
下記いずれかの式で表される、項1に記載する多環芳香族化合物。
Item 3. The polycyclic aromatic compound described in
項1~4のいずれかに記載する多環芳香族化合物を含有する、有機デバイス用材料。
A material for an organic device, comprising the polycyclic aromatic compound according to any one of
前記有機デバイス用材料が、有機電界発光素子用材料、有機電界効果トランジスタ用材料または有機薄膜太陽電池用材料である、項5に記載する有機デバイス用材料。 Item 6.
Item 6. The material for an organic device according to
発光層用材料である、項6に記載する有機電界発光素子用材料。 Item 7.
7. A material for an organic electroluminescent device according to item 6, which is a material for a light emitting layer.
さらに、下記一般式(2)で表される多環芳香族化合物および下記一般式(2)で表される構造を複数有する多環芳香族化合物の多量体の少なくとも1つを含有する、項7に記載する発光層用材料。
A環、B環およびC環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも1つの水素は置換されていてもよく、
X1およびX2はそれぞれ独立して>Oまたは>N-Rであり、前記>N-RのRは置換されていてもよいアリール、置換されていてもよいヘテロアリールまたはアルキルであり、また、前記N-RのRは連結基または単結合により前記A環、B環および/またはC環と結合していてもよく、そして、
式(2)で表される化合物または構造における少なくとも1つの水素がハロゲン、シアノまたは重水素で置換されていてもよい。) Item 8.
Item 7 further contains at least one of a polycyclic aromatic compound represented by the following General Formula (2) and a multimer of a polycyclic aromatic compound having a plurality of structures represented by the following General Formula (2), The material for the light emitting layer described in 4.
Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
X 1 and X 2 are each independently> O or> N—R, and R in the aforementioned> N—R is optionally substituted aryl, optionally substituted heteroaryl or alkyl, and And R in said NR may be bonded to said A ring, B ring and / or C ring by a linking group or a single bond, and
At least one hydrogen in the compound or structure represented by Formula (2) may be substituted with halogen, cyano or deuterium. )
陽極および陰極からなる一対の電極と、該一対の電極間に配置され、項7または8に記載する発光層用材料を含有する発光層とを有する、有機電界発光素子。 Item 9.
Item 9. An organic electroluminescent device comprising: a pair of electrodes consisting of an anode and a cathode; and a light emitting layer disposed between the pair of electrodes and containing the material for a light emitting layer described in item 7 or 8.
さらに、前記陰極と該発光層との間に配置される電子輸送層および/または電子注入層を有し、該電子輸送層および電子注入層の少なくとも1つは、ボラン誘導体、ピリジン誘導体、フルオランテン誘導体、BO系誘導体、アントラセン誘導体、ベンゾフルオレン誘導体、ホスフィンオキサイド誘導体、ピリミジン誘導体、カルバゾール誘導体、トリアジン誘導体、ベンゾイミダゾール誘導体、フェナントロリン誘導体、およびキノリノール系金属錯体からなる群から選択される少なくとも1つを含有する、項9に記載する有機電界発光素子。
Furthermore, it has an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridine derivative, a fluoranthene derivative , At least one selected from the group consisting of BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and
前記電子輸送層および/または電子注入層が、さらに、アルカリ金属、アルカリ土類金属、希土類金属、アルカリ金属の酸化物、アルカリ金属のハロゲン化物、アルカリ土類金属の酸化物、アルカリ土類金属のハロゲン化物、希土類金属の酸化物、希土類金属のハロゲン化物、アルカリ金属の有機錯体、アルカリ土類金属の有機錯体および希土類金属の有機錯体からなる群から選択される少なくとも1つを含有する、項10に記載の有機電界発光素子。 Item 11.
The electron transport layer and / or the electron injection layer may further be selected from alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, and alkaline earth metals.
項9~11のいずれかに記載する有機電界発光素子を備えた表示装置。 Item 12.
Item 12. A display device comprising the organic electroluminescent device according to any one of items 9 to 11.
項9~11のいずれかに記載する有機電界発光素子を備えた照明装置。 Item 13.
A lighting device comprising the organic electroluminescent device according to any one of Items 9 to 11.
本発明は、一般式(1)で表される多環芳香族化合物である。
一般式(1)で表される多環芳香族化合物は、基本的には、a環とb環およびc環とを結合基(X1およびX2)で結合させることで第1中間体を製造し(第1反応)、その後にa環にボロン酸エステル基を導入し(第2中間体)、さらに任意にこれを加水分解することでそのボロン酸(第2中間体)を製造した後(第2反応)、この第2中間体(ボロン酸またはボロン酸エステル)に塩化アルミニウムのようなルイス酸を反応させることで、製造することができる(第3反応)。 2. Process for Producing Polycyclic Aromatic Compound Represented by General Formula (1) The polycyclic aromatic compound represented by General Formula (1) basically has a linking group for the a ring, the b ring and the c ring. A first intermediate is produced by combining (X 1 and X 2 ) (first reaction), and then a boronate ester group is introduced to the a ring (second intermediate), and this is optionally hydrolyzed After the boronic acid (second intermediate) is produced by decomposition (second reaction), a Lewis acid such as aluminum chloride is reacted with the second intermediate (boronic acid or boronic ester), It can be produced (third reaction).
一般式(2)で表される多環芳香族化合物および一般式(2)で表される構造を複数有する多環芳香族化合物の多量体は、一般式(1)で表される多環芳香族化合物と組み合わせて発光層用材料として用いることができ、基本的にはドーパントとして機能する。当該多環芳香族化合物およびその多量体は、好ましくは、下記一般式(2’)で表される多環芳香族化合物、または下記一般式(2’)で表される構造を複数有する多環芳香族化合物の多量体である。
なお、一般式(2)や一般式(2’)の化合物およびその多量体は、一般式(1)で表される多環芳香族化合物とは異なる化合物であり、一般式(1)で表される多環芳香族化合物は一般式(2)や一般式(2’)の定義から除かれる。
In addition, the compound of General formula (2) or General formula (2 '), and its multimer are compounds different from the polycyclic aromatic compound represented by General formula (1), and are represented by General formula (1). The polycyclic aromatic compound to be substituted is excluded from the definition of the general formula (2) or the general formula (2 ').
A環、B環およびC環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも1つの水素は置換されていてもよく、
X1およびX2はそれぞれ独立して>Oまたは>N-Rであり、前記>N-RのRは置換されていてもよいアリール、置換されていてもよいヘテロアリールまたはアルキルであり、また、前記N-RのRは連結基または単結合により前記A環、B環および/またはC環と結合していてもよく、そして、
式(2)で表される化合物または構造における少なくとも1つの水素がハロゲン、シアノまたは重水素で置換されていてもよい。 In the above formula (2),
Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
X 1 and X 2 are each independently> O or> N—R, and R in the aforementioned> N—R is optionally substituted aryl, optionally substituted heteroaryl or alkyl, and And R in said NR may be bonded to said A ring, B ring and / or C ring by a linking group or a single bond, and
At least one hydrogen in the compound or structure represented by Formula (2) may be substituted with halogen, cyano or deuterium.
R1からR11は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、また、R1からR11のうちの隣接する基同士が結合してa環、b環またはc環と共にアリール環またはヘテロアリール環を形成していてもよく、形成された環における少なくとも1つの水素はアリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキル、アルコキシまたはアリールオキシで置換されていてもよく、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
X1およびX2はそれぞれ独立して>N-Rであり、前記>N-RのRは炭素数6~12のアリール、炭素数2~15のヘテロアリールまたは炭素数1~6のアルキルであり、また、前記>N-RのRは-O-、-S-、-C(-R)2-または単結合により前記a環、b環および/またはc環と結合していてもよく、前記-C(-R)2-のRは炭素数1~6のアルキルであり、そして、
式(2’)で表される化合物における少なくとも1つの水素がハロゲンまたは重水素で置換されていてもよい。 In the above formula (2 ′),
R 1 to R 11 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy or aryloxy, and at least one hydrogen in these is aryl, It may be substituted by heteroaryl or alkyl, and adjacent groups of R 1 to R 11 may be combined to form an aryl ring or heteroaryl ring together with the a ring, b ring or c ring. Also, at least one hydrogen in the formed ring may be substituted with aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, alkyl, alkoxy or aryloxy, and at least one of them is Hydrogen is Ally Optionally substituted with aryl, heteroaryl or alkyl,
X 1 and X 2 are each independently> N—R, and R in the above> N—R is aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, or alkyl having 1 to 6 carbons And R in> N—R may be bonded to the a ring, b ring and / or c ring via —O—, —S—, —C (—R) 2 — or a single bond. And R in -C (-R) 2- is alkyl having 1 to 6 carbon atoms, and
At least one hydrogen in the compound represented by the formula (2 ′) may be substituted with halogen or deuterium.
この規定は、下記式(2’-3-1)で表される、X1やX2が縮合環B’および縮合環C’に取り込まれた環構造を有する化合物で表現できる。すなわち、例えば一般式(2’)におけるb環(またはc環)であるベンゼン環に対してX1(またはX2)を取り込むようにして他の環が縮合して形成されるB’環(またはC’環)を有する化合物である。この化合物は、例えば後述する具体的化合物として列挙した、式(2-451)~式(2-462)で表されるような化合物および式(2-1401)~式(2-1460)で表されるような化合物に対応し、形成されてできた縮合環B’(または縮合環C’)は例えばフェノキサジン環、フェノチアジン環またはアクリジン環である。
また、上記規定は、下記式(2’-3-2)や式(2’-3-3)で表される、X1および/またはX2が縮合環A’に取り込まれた環構造を有する化合物でも表現できる。すなわち、例えば一般式(2’)におけるa環であるベンゼン環に対してX1(および/またはX2)を取り込むようにして他の環が縮合して形成されるA’環を有する化合物である。この化合物は、例えば後述する具体的化合物として列挙した式(2-471)~式(2-479)で表されるような化合物に対応し、形成されてできた縮合環A’は例えばフェノキサジン環、フェノチアジン環またはアクリジン環である。なお、下記式(2’-3-1)、式(2’-3-2)および式(2’-3-3)中のR1~R11、a、b、c、X1およびX2の定義は一般式(2’)における定義と同じである。 Here, the definition of “in R of> N—R is bonded to the ring A, ring B and / or ring C via a linking group or a single bond” in the general formula (2) is a general formula (2 ′) In the above, the definition that “in R of> N—R is bound to the a ring, b ring and / or c ring by —O—, —S—, —C (—R) 2 — or a single bond” Corresponds to
This definition can be expressed as a compound represented by the following formula (2′-3-1), which has a ring structure in which X 1 or X 2 is incorporated into fused ring B ′ and fused ring C ′. That is, for example, B ′ ring formed by condensation of other rings such that X 1 (or X 2 ) is incorporated to a benzene ring which is ring b (or ring c) in the general formula (2 ′) Or a compound having a C 'ring). This compound is, for example, a compound represented by Formula (2-451) to Formula (2-462) and a compound represented by Formula (2-1401) to Formula (2-1460) listed as specific compounds described later. The fused ring B '(or fused ring C') formed and formed corresponding to the compound as such is for example a phenoxazine ring, a phenothiazine ring or an acridine ring.
Further, the above definition is a ring structure in which X 1 and / or X 2 is incorporated into the fused ring A ′, which is represented by the following formula (2′-3-2) or the formula (2′-3-3) It can express also with the compound which it has. That is, for example, a compound having an A ′ ring formed by condensation of other rings such that X 1 (and / or X 2 ) is incorporated into the benzene ring which is a ring in the general formula (2 ′) is there. This compound corresponds to, for example, the compounds represented by Formula (2-471) to Formula (2-479) listed as specific compounds described later, and the fused ring A 'formed is, for example, phenoxazine Ring, phenothiazine ring or acridine ring. R 1 to R 11 , a, b, c, X 1 and X in the following formula (2′-3-1), formula (2′-3-2) and formula (2′-3-3) The definition of 2 is the same as the definition in General Formula (2 ').
R1、R3、R4~R7、R8~R11およびR12~R15は、それぞれ独立して、水素、アリール、ヘテロアリール、ジアリールアミノ、ジヘテロアリールアミノ、アリールヘテロアリールアミノ、アルキル、アルコキシまたはアリールオキシであり、これらにおける少なくとも1つの水素はアリール、ヘテロアリールまたはアルキルで置換されていてもよく、
X1は-O-または>N-Rであり、前記>N-RのRは炭素数6~12のアリール、炭素数2~15のヘテロアリールまたは炭素数1~6のアルキルであり、これらにおける少なくとも1つの水素は炭素数6~12のアリール、炭素数2~15のヘテロアリールまたは炭素数1~6のアルキルで置換されていてもよく、
Z1およびZ2は、それぞれ独立して、アリール、ヘテロアリール、ジアリールアミノ、アリールオキシ、アリール置換アルキル、水素、アルキルまたはアルコキシであり、これらにおける少なくとも1つの水素はアルキルで置換されていてもよく、Z1が、アルキルで置換されていてもよいフェニル、アルキルで置換されていてもよいm-ビフェニリル、アルキルで置換されていてもよいp-ビフェニリル、アルキルで置換されていてもよい単環系ヘテロアリール、アルキルで置換されていてもよいジフェニルアミノ、水素、アルキルまたはアルコキシである場合は、Z2は水素、アルキルまたはアルコキシであることはなく、そして、
式(2”)で表される化合物における少なくとも1つの水素がハロゲンまたは重水素で置換されていてもよい。 In the above formula (2 ′ ′),
R 1 , R 3 , R 4 to R 7 , R 8 to R 11 and R 12 to R 15 are each independently hydrogen, aryl, heteroaryl, diarylamino, diheteroarylamino, arylheteroarylamino, Alkyl, alkoxy or aryloxy, wherein at least one hydrogen may be substituted with aryl, heteroaryl or alkyl;
X 1 is —O— or> N—R, and R in> N—R is aryl having 6 to 12 carbon atoms, heteroaryl having 2 to 15 carbon atoms, or alkyl having 1 to 6 carbon atoms, At least one hydrogen in the above may be substituted with aryl having 6 to 12 carbons, heteroaryl having 2 to 15 carbons, or alkyl having 1 to 6 carbons,
Z 1 and Z 2 are each independently aryl, heteroaryl, diarylamino, aryloxy, aryl-substituted alkyl, hydrogen, alkyl or alkoxy, and at least one hydrogen in these may be substituted with alkyl And Z 1 is optionally substituted phenyl, optionally substituted alkyl, m-biphenylyl, optionally substituted alkyl p-biphenylyl, optionally substituted alkyl, monocyclic system When it is heteroaryl, diphenylamino optionally substituted with alkyl, hydrogen, alkyl or alkoxy, Z 2 can not be hydrogen, alkyl or alkoxy, and
At least one hydrogen in the compound represented by the formula (2 ′ ′) may be substituted with halogen or deuterium.
すなわち、Z1として、アリールの中でもフェニル基、m-ビフェニリル基およびp-ビフェニリル基、ヘテロアリールの中でも単環系ヘテロアリール基(ピリジル基などの1つの環で構成されるヘテロアリール基)、ジアリールアミノの中でもジフェニルアミノ基、水素、アルキル基およびアルコキシ基、そしてこれらの基における少なくとも1つの水素がアルキルで置換された基は、単独では本願における嵩高い置換基としての役割を有さないため、置換基Z2を嵩高くする必要がある。Z2としては、水素、アルキル基およびアルコキシ基、そしてこれらの基における少なくとも1つの水素がアルキルで置換された基が嵩高くないため、これらのZ1とZ2との組み合わせは本願からは除かれる。
Z1は、好ましくは、o-ビフェニリル基、o-ナフチルフェニル基(フェニル基のオルト位に1-または2-ナフチル基が置換した基)、フェニルナフチルアミノ基、ジナフチルアミノ基、フェニルオキシ基、トリフェニルメチル基(トリチル基)、およびこれらの基の少なくとも1つがアルキル(例えばメチル、エチル、i-プロピルまたはt-ブチル、好ましくはメチルまたはt-ブチル、より好ましくはt-ブチル)で置換された基である。
Z2は、好ましくは、フェニル基、1-または2-ナフチル基、およびこれらの基の少なくとも1つがアルキル(例えばメチル、エチル、i-プロピルまたはt-ブチル、好ましくはメチルまたはt-ブチル、より好ましくはt-ブチル)で置換された基である。 However, even if a phenyl group is selected at the position of Z 1 , it does not become a bulky substituent, but the position of Z 2 is the ortho position in> N-phenyl group where the surrounding space is restricted. even a one phenyl group not a bulky substituent has a role as a bulky substituent at the position of Z 2. Thus, as the groups having different bulk height effects depending on the position (groups having no function as bulky substituents at the Z 1 position), in addition to the phenyl group, m-biphenylyl group and p-biphenylyl group And monocyclic heteroaryl groups (heteroaryl groups composed of one ring such as pyridyl group) and diphenylamino group. Also, hydrogen, an alkyl group and an alkoxy group do not become bulky substituents as Z 1 or Z 2 .
That is, as Z 1 , among aryl, a phenyl group, m-biphenylyl group and p-biphenylyl group, among heteroaryls, monocyclic heteroaryl group (heteroaryl group composed of one ring such as pyridyl group), diaryl Among amino, a diphenylamino group, hydrogen, an alkyl group and an alkoxy group, and a group in which at least one hydrogen in these groups is substituted with an alkyl group alone do not have a role as a bulky substituent in the present application, It is necessary to make substituent Z 2 bulky. As Z 2 , hydrogen, an alkyl group and an alkoxy group, and a group in which at least one of the hydrogens in these groups is substituted with alkyl are not bulky, these Z 1 and Z 2 combinations are excluded from the present application. It is eaten.
Z 1 is preferably o-biphenylyl group, o-naphthylphenyl group (group in which 1- or 2-naphthyl group is substituted at the ortho position of phenyl group), phenylnaphthylamino group, dinaphthylamino group, phenyloxy group , Triphenylmethyl group (trityl group), and at least one of these groups is substituted with alkyl (eg methyl, ethyl, i-propyl or t-butyl, preferably methyl or t-butyl, more preferably t-butyl) Is a group that is
Z 2 is preferably a phenyl group, 1- or 2-naphthyl group, and at least one of these groups is alkyl (eg methyl, ethyl, i-propyl or t-butyl, preferably methyl or t-butyl, Preferred is a group substituted with t-butyl).
なお、式中のRはアルキルであり、直鎖および分枝鎖のいずれでもよく、例えば、炭素数1~24の直鎖アルキルまたは炭素数3~24の分枝鎖アルキルがあげられる。炭素数1~18のアルキル(炭素数3~18の分枝鎖アルキル)が好ましく、炭素数1~12のアルキル(炭素数3~12の分枝鎖アルキル)がより好ましく、炭素数1~6のアルキル(炭素数3~6の分枝鎖アルキル)がさらに好ましく、炭素数1~4のアルキル(炭素数3~4の分枝鎖アルキル)が特に好ましい。また、Rとしては他にフェニルがあげられる。
また、「PhO-」はフェニルオキシ基であり、このフェニルは直鎖または分枝鎖のアルキルで置換されていてもよく、例えば、炭素数1~24の直鎖アルキルまたは炭素数3~24の分枝鎖アルキル、炭素数1~18のアルキル(炭素数3~18の分枝鎖アルキル)、炭素数1~12のアルキル(炭素数3~12の分枝鎖アルキル)、炭素数1~6のアルキル(炭素数3~6の分枝鎖アルキル)、炭素数1~4のアルキル(炭素数3~4の分枝鎖アルキル)で置換されていてもよい。 As such specific examples, for example, compounds represented by the following formulas (2-4501) to (2-4522) can be mentioned.
R in the formula is alkyl, and may be linear or branched, and examples thereof include linear alkyl having 1 to 24 carbon atoms and branched alkyl having 3 to 24 carbon atoms. Alkyl having 1 to 18 carbons (branched alkyl having 3 to 18 carbons) is preferable, and alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons) is more preferable, and ones having 1 to 6 carbons Alkyl (branched alkyl having 3 to 6 carbon atoms) are more preferable, and alkyl having 1 to 4 carbons (branched alkyl having 3 to 4 carbon atoms) is particularly preferable. In addition, another example of R is phenyl.
In addition, “PhO-” is a phenyloxy group, and this phenyl may be substituted with linear or branched alkyl, for example, linear alkyl having 1 to 24 carbons or 3 to 24 carbons. Branched alkyl, alkyl having 1 to 18 carbons (branched alkyl having 3 to 18 carbons), alkyl having 1 to 12 carbons (branched alkyl having 3 to 12 carbons), 1 to 6 carbons And C.sub.6-C 6 branched alkyl) and C.sub.1-C.sub.4 alkyl (C.sub.3-
具体的には、以下の化合物があげられる。下記式中のRはそれぞれ独立して炭素数1~12のアルキルまたは炭素数6~10のアリール、好ましくは炭素数1~4のアルキルまたはフェニルであり、nはそれぞれ独立して0~2、好ましくは1である。 Further, as specific examples of the compound represented by the formula (2) and the multimer thereof, in the above-mentioned compound, one or more of at least one hydrogen in one or a plurality of aromatic rings in the compound are mentioned And compounds substituted with alkyl or aryl, and more preferably compounds substituted with 1 to 2 carbons having 1 to 12 carbons or aryls having 6 to 10 carbons.
Specifically, the following compounds may be mentioned. R in the following formulas is each independently alkyl of 1 to 12 carbons or aryl of 6 to 10 carbons, preferably alkyl or phenyl of 1 to 4 carbons, and n is independently 0 to 2, Preferably it is 1.
一般式(2)や(2’)で表される多環芳香族化合物およびその多量体は、基本的には、まずA環(a環)とB環(b環)およびC環(c環)とを結合基(X1やX2を含む基)で結合させることで中間体を製造し(第1反応)、その後に、A環(a環)、B環(b環)およびC環(c環)を結合基(中心原子「B」(ホウ素)を含む基)で結合させることで最終生成物を製造することができる(第2反応)。 4. Process for Producing Polycyclic Aromatic Compound Represented by General Formula (2) and Multimer Thereof A polycyclic aromatic compound represented by General Formula (2) or (2 ′) and a multimer thereof are basically First, an intermediate is produced by combining A ring (a ring) with B ring (b ring) and C ring (c ring) by a linking group (group containing X 1 and X 2 ) (first reaction) And then the A ring (a ring), the B ring (b ring) and the C ring (c ring) with a linking group (a group containing a central atom “B” (boron)) to obtain the final product It can be produced (second reaction).
本発明に係る多環芳香族化合物は、有機デバイス用材料として用いることができる。有機デバイスとしては、例えば、有機電界発光素子、有機電界効果トランジスタまたは有機薄膜太陽電池などが挙げられる。 5. Organic Device The polycyclic aromatic compound according to the present invention can be used as a material for an organic device. As an organic device, an organic electroluminescent element, an organic field effect transistor, an organic thin film solar cell etc. are mentioned, for example.
一般式(1)で表される多環芳香族化合物は、例えば、有機電界発光素子の材料として用いることができる。以下に、本実施形態に係る有機EL素子について図面に基づいて詳細に説明する。図1は、本実施形態に係る有機EL素子を示す概略断面図である。 5-1. The polycyclic aromatic compound represented by organic electroluminescent element General formula (1) can be used as a material of an organic electroluminescent element, for example. Below, the organic EL element which concerns on this embodiment is demonstrated in detail based on drawing. FIG. 1 is a schematic cross-sectional view showing the organic EL element according to the present embodiment.
図1に示された有機電界発光素子100は、基板101と、基板101上に設けられた陽極102と、陽極102の上に設けられた正孔注入層103と、正孔注入層103の上に設けられた正孔輸送層104と、正孔輸送層104の上に設けられた発光層105と、発光層105の上に設けられた電子輸送層106と、電子輸送層106の上に設けられた電子注入層107と、電子注入層107の上に設けられた陰極108とを有する。 <Structure of Organic Electroluminescent Device>
The
基板101は、有機電界発光素子100の支持体であり、通常、石英、ガラス、金属、プラスチックなどが用いられる。基板101は、目的に応じて板状、フィルム状、またはシート状に形成され、例えば、ガラス板、金属板、金属箔、プラスチックフィルム、プラスチックシートなどが用いられる。なかでも、ガラス板、および、ポリエステル、ポリメタクリレート、ポリカーボネート、ポリスルホンなどの透明な合成樹脂製の板が好ましい。ガラス基板であれば、ソーダライムガラスや無アルカリガラスなどが用いられ、また、厚みも機械的強度を保つのに十分な厚みがあればよいので、例えば、0.2mm以上あればよい。厚さの上限値としては、例えば、2mm以下、好ましくは1mm以下である。ガラスの材質については、ガラスからの溶出イオンが少ない方がよいので無アルカリガラスの方が好ましいが、SiO2などのバリアコートを施したソーダライムガラスも市販されているのでこれを使用することができる。また、基板101には、ガスバリア性を高めるために、少なくとも片面に緻密なシリコン酸化膜などのガスバリア膜を設けてもよく、特にガスバリア性が低い合成樹脂製の板、フィルムまたはシートを基板101として用いる場合にはガスバリア膜を設けるのが好ましい。 <Substrate in Organic Electroluminescent Device>
The substrate 101 is a support of the
陽極102は、発光層105へ正孔を注入する役割を果たす。なお、陽極102と発光層105との間に正孔注入層103および/または正孔輸送層104が設けられている場合には、これらを介して発光層105へ正孔を注入することになる。 <Anode in Organic Electroluminescent Device>
The
正孔注入層103は、陽極102から移動してくる正孔を、効率よく発光層105内または正孔輸送層104内に注入する役割を果たす。正孔輸送層104は、陽極102から注入された正孔または陽極102から正孔注入層103を介して注入された正孔を、効率よく発光層105に輸送する役割を果たす。正孔注入層103および正孔輸送層104は、それぞれ、正孔注入・輸送材料の一種または二種以上を積層、混合するか、正孔注入・輸送材料と高分子結着剤の混合物により形成される。また、正孔注入・輸送材料に塩化鉄(III)のような無機塩を添加して層を形成してもよい。 <Hole Injection Layer in Organic Electroluminescent Device, Hole Transport Layer>
The
発光層105は、電界を与えられた電極間において、陽極102から注入された正孔と、陰極108から注入された電子とを再結合させることにより発光する層である。発光層105を形成する材料としては、正孔と電子との再結合によって励起されて発光する化合物(発光性化合物)であればよく、安定な薄膜形状を形成することができ、かつ、固体状態で強い発光(蛍光)効率を示す化合物であるのが好ましい。例えば、ホスト材料として上記一般式(1)で表される多環芳香族化合物と、ドーパント材料として上記一般式(2)で表される多環芳香族化合物またはその多量体を含有する発光層用材料を用いることができる。 <Light emitting layer in organic electroluminescent device>
The light emitting layer 105 is a layer that emits light by recombining holes injected from the
また、特開2003-347056号公報、および特開2001-307884号公報などに記載されたスチルベン構造を有するアミンを用いてもよい。 Specific examples of amines having stilbene structure are N, N, N ', N'-tetra (4-biphenylyl) -4,4'-diaminostilbene, N, N, N', N'-tetra (1-naphthyl) ) -4,4′-diaminostilbene, N, N, N ′, N′-tetra (2-naphthyl) -4,4′-diaminostilbene, N, N′-di (2-naphthyl) -N, N '-Diphenyl-4,4'-diaminostilbene, N, N'-di (9-phenanthryl) -N, N'-diphenyl-4,4'-diaminostilbene, 4,4'-bis [4 "-bis (Diphenylamino) styryl] -biphenyl, 1,4-bis [4'-bis (diphenylamino) styryl] -benzene, 2,7-bis [4'-bis (diphenylamino) styryl] -9,9-dimethyl Fluorene, 4,4'-bis (9-ethyl-3-cal) And bazovinylene) -biphenyl, 4,4'-bis (9-phenyl-3-carbazovinylene) -biphenyl and the like.
Further, amines having a stilbene structure described in JP-A-2003-349056, JP-A-2001-307884, etc. may be used.
また、特開平11-97178号公報、特開2000-133457号公報、特開2000-26324号公報、特開2001-267079号公報、特開2001-267078号公報、特開2001-267076号公報、特開2000-34234号公報、特開2001-267075号公報、および特開2001-217077号公報などに記載されたペリレン誘導体を用いてもよい。 Examples of perylene derivatives include, for example, 3,10-bis (2,6-dimethylphenyl) perylene, 3,10-bis (2,4,6-trimethylphenyl) perylene, 3,10-diphenylperylene, 3,4- Diphenylperylene, 2,5,8,11-tetra-t-butylperylene, 3,4,9,10-tetraphenylperylene, 3- (1'-pyrenyl) -8,11-di (t-butyl) perylene 3- (9'-anthryl) -8,11-di (t-butyl) perylene, 3,3'-bis (8,11-di (t-butyl) perylenyl) and the like.
Further, JP-A-11-97178, JP-A-2000-133457, JP-A-2000-26324, JP-A-2001-267079, JP-A-2001-267078, JP-A-2001-267076, Perylene derivatives described in JP-A-2000-34234, JP-A-2001-267075, and JP-A-2001-217077 may be used.
また、国際公開第2000/40586号パンフレットなどに記載されたボラン誘導体を用いてもよい。 Examples of borane derivatives include 1,8-diphenyl-10- (dimesitylboryl) anthracene, 9-phenyl-10- (dimesitylboryl) anthracene, 4- (9'-anthryl) dimesitylborylnaphthalene, 4- (10 ') -Phenyl-9'-anthryl) dimesitylborylnaphthalene, 9- (dimesitylboryl) anthracene, 9- (4'-biphenylyl) -10- (dimesitylboryl) anthracene, 9- (4 '-(N-carbazolyl) phenyl) And -10- (dimesitylboryl) anthracene.
In addition, borane derivatives described in WO 2000/40586 and the like may be used.
また、特開2006-156888号公報などに記載された芳香族アミン誘導体を用いてもよい。 In addition to the above, [4- (4-diphenylamino-phenyl) naphthalen-1-yl] -diphenylamine, [6- (4-diphenylamino-phenyl) naphthalen-2-yl] -diphenylamine, 4,4 ′ -Bis [4-diphenylaminonaphthalen-1-yl] biphenyl, 4,4'-bis [6-diphenylaminonaphthalen-2-yl] biphenyl, 4,4 "-bis [4-diphenylaminonaphthalen-1-yl] ] -P-terphenyl, 4,4 ′ ′-bis [6-diphenylaminonaphthalen-2-yl] -p-terphenyl and the like.
In addition, aromatic amine derivatives described in JP-A-2006-156888 may be used.
また、特開2004-43646号公報、特開2001-76876号公報、および特開平6-298758号公報などに記載されたクマリン誘導体を用いてもよい。 Examples of coumarin derivatives include coumarin-6, coumarin-334 and the like.
In addition, coumarin derivatives described in JP-A-2004-43646, JP-A-2001-76876, and JP-A-6-298758 may be used.
電子注入層107は、陰極108から移動してくる電子を、効率よく発光層105内または電子輸送層106内に注入する役割を果たす。電子輸送層106は、陰極108から注入された電子または陰極108から電子注入層107を介して注入された電子を、効率よく発光層105に輸送する役割を果たす。電子輸送層106および電子注入層107は、それぞれ、電子輸送・注入材料の一種または二種以上を積層、混合するか、電子輸送・注入材料と高分子結着剤の混合物により形成される。 <Electron Injection Layer in Organic Electroluminescent Device, Electron Transport Layer>
The
ボラン誘導体は、例えば下記一般式(ETM-1)で表される化合物であり、詳細には特開2007-27587号公報に開示されている。
The borane derivative is, for example, a compound represented by the following general formula (ETM-1), and is disclosed in detail in JP-A-2007-27587.
ピリジン誘導体は、例えば下記式(ETM-2)で表される化合物であり、好ましくは式(ETM-2-1)または式(ETM-2-2)で表される化合物である。
The pyridine derivative is, for example, a compound represented by the following formula (ETM-2), preferably a compound represented by the formula (ETM-2-1) or the formula (ETM-2-2).
具体的な「シクロアルキル」としては、シクロプロピル、シクロブチル、シクロペンチル、シクロヘキシル、メチルシクロペンチル、シクロヘプチル、メチルシクロヘキシル、シクロオクチルまたはジメチルシクロヘキシルなどが挙げられる。 Examples of “cycloalkyl” in R 11 to R 18 include cycloalkyl having 3 to 12 carbon atoms. Preferred "cycloalkyl" is cycloalkyl having 3 to 10 carbon atoms. More preferable "cycloalkyl" is cycloalkyl having 3 to 8 carbon atoms. More preferable "cycloalkyl" is cycloalkyl having 3 to 6 carbon atoms.
Specific "cycloalkyl" includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, methylcyclopentyl, cycloheptyl, methylcyclohexyl, cyclooctyl or dimethylcyclohexyl and the like.
フルオランテン誘導体は、例えば下記一般式(ETM-3)で表される化合物であり、詳細には国際公開第2010/134352号公報に開示されている。
The fluoranthene derivative is, for example, a compound represented by the following general formula (ETM-3), and is specifically disclosed in WO 2010/134352.
BO系誘導体は、例えば下記式(ETM-4)で表される多環芳香族化合物、または下記式(ETM-4)で表される構造を複数有する多環芳香族化合物の多量体である。
The BO-based derivative is, for example, a multimer of a polycyclic aromatic compound represented by the following formula (ETM-4) or a polycyclic aromatic compound having a plurality of structures represented by the following formula (ETM-4).
アントラセン誘導体の一つは、例えば下記式(ETM-5-1)で表される化合物である。
One of the anthracene derivatives is, for example, a compound represented by the following formula (ETM-5-1).
ベンゾフルオレン誘導体は、例えば下記式(ETM-6)で表される化合物である。
The benzofluorene derivative is, for example, a compound represented by the following formula (ETM-6).
ホスフィンオキサイド誘導体は、例えば下記式(ETM-7-1)で表される化合物である。詳細は国際公開第2013/079217号公報にも記載されている。
R6は、CN、置換または無置換の、炭素数1~20のアルキル、炭素数1~20のヘテロアルキル、炭素数6~20のアリール、炭素数5~20のヘテロアリール、炭素数1~20のアルコキシまたは炭素数6~20のアリールオキシであり、
R7およびR8は、それぞれ独立して、置換または無置換の、炭素数6~20のアリールまたは炭素数5~20のヘテロアリールであり、
R9は酸素または硫黄であり、
jは0または1であり、kは0または1であり、rは0~4の整数であり、qは1~3の整数である。 <Phosphine oxide derivative>
The phosphine oxide derivative is, for example, a compound represented by the following formula (ETM-7-1). The details are also described in WO 2013/079217.
R 6 represents CN, substituted or unsubstituted alkyl having 1 to 20 carbons, heteroalkyl having 1 to 20 carbons, aryl having 6 to 20 carbons, heteroaryl having 5 to 20 carbons, or 1 to 6 carbons 20 alkoxy or aryloxy having 6 to 20 carbon atoms,
R 7 and R 8 are each independently substituted or unsubstituted aryl having 6 to 20 carbon atoms or heteroaryl having 5 to 20 carbon atoms,
R 9 is oxygen or sulfur,
j is 0 or 1, k is 0 or 1, r is an integer of 0 to 4, and q is an integer of 1 to 3.
ピリミジン誘導体は、例えば下記式(ETM-8)で表される化合物であり、好ましくは下記式(ETM-8-1)で表される化合物である。詳細は国際公開第2011/021689号公報にも記載されている。
The pyrimidine derivative is, for example, a compound represented by the following formula (ETM-8), and preferably a compound represented by the following formula (ETM-8-1). The details are also described in International Publication No. WO 2011/01689.
カルバゾール誘導体は、例えば下記式(ETM-9)で表される化合物、またはそれが単結合などで複数結合した多量体である。詳細は米国公開公報2014/0197386号公報に記載されている。
The carbazole derivative is, for example, a compound represented by the following formula (ETM-9), or a multimer in which a plurality of compounds are linked via a single bond or the like. Details are described in US Patent Publication No. 2014/0197386.
トリアジン誘導体は、例えば下記式(ETM-10)で表される化合物であり、好ましくは下記式(ETM-10-1)で表される化合物である。詳細は米国公開公報2011/0156013号公報に記載されている。
The triazine derivative is, for example, a compound represented by the following formula (ETM-10), and preferably a compound represented by the following formula (ETM-10-1). Details are described in U.S. Patent Publication No. 2011/0156013.
ベンゾイミダゾール誘導体は、例えば下記式(ETM-11)で表される化合物である。
The benzimidazole derivative is, for example, a compound represented by the following formula (ETM-11).
フェナントロリン誘導体は、例えば下記式(ETM-12)または式(ETM-12-1)で表される化合物である。詳細は国際公開2006/021982号公報に記載されている。
The phenanthroline derivative is, for example, a compound represented by the following formula (ETM-12) or the formula (ETM-12-1). Details are described in WO2006 / 021982.
キノリノール系金属錯体は、例えば下記一般式(ETM-13)で表される化合物である。
The quinolinol metal complex is, for example, a compound represented by the following general formula (ETM-13).
チアゾール誘導体は、例えば下記式(ETM-14-1)で表される化合物である。
The thiazole derivative is, for example, a compound represented by the following formula (ETM-14-1).
陰極108は、電子注入層107および電子輸送層106を介して、発光層105に電子を注入する役割を果たす。 <Cathode in Organic Electroluminescent Device>
The
以上の正孔注入層、正孔輸送層、発光層、電子輸送層および電子注入層に用いられる材料は単独で各層を形成することができるが、高分子結着剤としてポリ塩化ビニル、ポリカーボネート、ポリスチレン、ポリ(N-ビニルカルバゾール)、ポリメチルメタクリレート、ポリブチルメタクリレート、ポリエステル、ポリスルホン、ポリフェニレンオキサイド、ポリブタジエン、炭化水素樹脂、ケトン樹脂、フェノキシ樹脂、ポリアミド、エチルセルロース、酢酸ビニル樹脂、ABS樹脂、ポリウレタン樹脂などの溶剤可溶性樹脂や、フェノール樹脂、キシレン樹脂、石油樹脂、ユリア樹脂、メラミン樹脂、不飽和ポリエステル樹脂、アルキド樹脂、エポキシ樹脂、シリコーン樹脂などの硬化性樹脂などに分散させて用いることも可能である。 <Binder which may be used in each layer>
The materials used for the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer, and the electron injection layer described above can form each layer independently, but polyvinyl chloride, polycarbonate, or the like as a polymer binder Polystyrene, poly (N-vinylcarbazole), polymethyl methacrylate, polybutyl methacrylate, polyester, polysulfone, polyphenylene oxide, polybutadiene, hydrocarbon resin, ketone resin, phenoxy resin, polyamide, ethyl cellulose, vinyl acetate resin, ABS resin, polyurethane resin Etc., and can be used by dispersing it in a solvent-soluble resin such as phenol resin, xylene resin, petroleum resin, urea resin, melamine resin, unsaturated polyester resin, alkyd resin, epoxy resin, silicone resin, etc. is there.
有機電界発光素子を構成する各層は、各層を構成すべき材料を蒸着法、抵抗加熱蒸着、電子ビーム蒸着、スパッタリング、分子積層法、印刷法、スピンコート法またはキャスト法、コーティング法などの方法で薄膜とすることにより、形成することができる。このようにして形成された各層の膜厚については特に限定はなく、材料の性質に応じて適宜設定することができるが、通常2nm~5000nmの範囲である。膜厚は通常、水晶発振式膜厚測定装置などで測定できる。蒸着法を用いて薄膜化する場合、その蒸着条件は、材料の種類、膜の目的とする結晶構造および会合構造などにより異なる。蒸着条件は一般的に、蒸着用ルツボの加熱温度+50~+400℃、真空度10-6~10-3Pa、蒸着速度0.01~50nm/秒、基板温度-150~+300℃、膜厚2nm~5μmの範囲で適宜設定することが好ましい。 <Method of Manufacturing Organic Electroluminescent Device>
Each layer constituting the organic electroluminescent element is formed of a material to be constituted of each layer by a method such as evaporation, resistance heating evaporation, electron beam evaporation, sputtering, molecular lamination, printing, spin coating or casting, or the like. It can be formed by using a thin film. There is no particular limitation on the film thickness of each layer formed in this way, and it can be appropriately set according to the property of the material, but it is usually in the range of 2 nm to 5000 nm. The film thickness can usually be measured by a crystal oscillation type film thickness measuring device or the like. In the case of thin film formation using a vapor deposition method, the vapor deposition conditions differ depending on the type of material, the desired crystal structure and association structure of the film, and the like. The deposition conditions are generally as follows: heating temperature of the deposition crucible + 50 to + 400 ° C, degree of
また、本発明は、有機電界発光素子を備えた表示装置または有機電界発光素子を備えた照明装置などにも応用することができる。
有機電界発光素子を備えた表示装置または照明装置は、本実施形態にかかる有機電界発光素子と公知の駆動装置とを接続するなど公知の方法によって製造することができ、直流駆動、パルス駆動、交流駆動など公知の駆動方法を適宜用いて駆動することができる。 <Application Example of Organic Electroluminescent Device>
The present invention can also be applied to a display device provided with an organic electroluminescent device or a lighting device provided with an organic electroluminescent device.
The display device or the illumination device provided with the organic electroluminescent device can be manufactured by a known method such as connecting the organic electroluminescent device according to the present embodiment and a known drive device, and can be DC drive, pulse drive, AC It can drive, using suitably well-known drive methods, such as a drive.
本発明に係る多環芳香族化合物は、上述した有機電界発光素子の他に、有機電界効果トランジスタまたは有機薄膜太陽電池などの作製に用いることができる。 5-2. Other Organic Devices The polycyclic aromatic compound according to the present invention can be used for the production of an organic field effect transistor, an organic thin film solar cell, etc. in addition to the organic electroluminescent device described above.
(1)基板/ゲート電極/絶縁体層/ソース電極・ドレイン電極/有機半導体活性層
(2)基板/ゲート電極/絶縁体層/有機半導体活性層/ソース電極・ドレイン電極
(3)基板/有機半導体活性層/ソース電極・ドレイン電極/絶縁体層/ゲート電極
(4)基板/ソース電極・ドレイン電極/有機半導体活性層/絶縁体層/ゲート電極
このように構成された有機電界効果トランジスタは、アクティブマトリックス駆動方式の液晶ディスプレイや有機エレクトロルミネッセンスディスプレイの画素駆動スイッチング素子などとして適用できる。 In the structure of the organic field effect transistor, generally, a source electrode and a drain electrode are provided in contact with the organic semiconductor active layer formed using the polycyclic aromatic compound according to the present invention, and further in contact with the organic semiconductor active layer. The gate electrode may be provided with the insulating layer (dielectric layer) interposed therebetween. Examples of the element structure include the following structures.
(1) substrate / gate electrode / insulator layer / source electrode / drain electrode / organic semiconductor active layer (2) substrate / gate electrode / insulator layer / organic semiconductor active layer / source electrode / drain electrode (3) substrate / organic Semiconductor active layer / source electrode / drain electrode / insulator layer / gate electrode (4) substrate / source electrode / drain electrode / organic semiconductor active layer / insulator layer / gate electrode The organic field effect transistor configured in this way is The present invention can be applied as a pixel drive switching element of a liquid crystal display of an active matrix drive system or an organic electroluminescence display.
化合物(1-1):3-(10-フェニルアントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of compound (1-1): 3- (10-phenylanthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.88~8.85(m,1H)、8.83~8.80(m,1H)、7.83~7.65(m,7H)、7.63~7.50(m,7H)、7.48~7.42(m,1H)、7.40~7.34(m,4H)、7.32~7.24(m,2H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.88 to 8.85 (m, 1 H), 8.83 to 8.80 (m, 1 H), 7.83 to 7.65 (m, 7 H) ), 7.63 to 7.50 (m, 7H), 7.48 to 7.42 (m, 1H), 7.40 to 7.34 (m, 4H), 7.32 to 7.24 (m) , 2H).
化合物(1-2):12-(10-フェニルアントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-2): 12- (10-phenylanthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
MS(ACPI) m/z=523(M+H) The compound obtained by LC-MS measurement was confirmed to be the desired product.
MS (ACPI) m / z = 523 (M + H)
1H-NMR(400MHz,CDCl3):δ=8.81~8.79(m,1H)、8.51~8.47(m,1H)、7.90~7.74(m,7H)、7.67~7.51(m,7H)、7.40~7.33(m,5H)、7.32~7.28(m,1H)、7.21~7.16(m,1H). In addition, the structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.81 to 8.79 (m, 1 H), 8.51 to 8.47 (m, 1 H), 7.90 to 7.74 (m, 7 H) ), 7.67 to 7.51 (m, 7 H), 7.40 to 7.33 (m, 5 H), 7.32 to 7.28 (m, 1 H), 7.21 to 7.16 (m) , 1 H).
化合物(1-4):6-(10-フェニルアントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-4): 6- (10-phenylanthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.69(dd,2H)、7.79(t,1H)、7.70(ddd,2H)、7.54(dt,2H)、7.38(ddd,2H)、7.22(d,2H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.69 (dd, 2H), 7.79 (t, 1H), 7.70 (ddd, 2H), 7.54 (dt, 2H), 7 38 (ddd, 2H), 7.22 (d, 2H).
1H-NMR(400MHz,CDCl3):δ=8.80~8.70(m,2H)、7.90~7.85(m,1H)、7.82~7.75(m,3H)、7.75~7.53(m,7H)、7.53~7.43(m,4H)、7.37~7.26(m,5H)、6.92~6.88(m,1H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.80 to 8.70 (m, 2H), 7.90 to 7.85 (m, 1H), 7.82 to 7.75 (m, 3H) 7.75 to 7.53 (m, 7H), 7.53 to 7.43 (m, 4H), 7.37 to 7.26 (m, 5H), 6.92 to 6.88 (m) , 1 H).
化合物(1-3):4-(10-フェニルアントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-3): 4- (10-phenylanthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.97~8.93(m,1H)、8.87~8.83(m,1H)、7.80~7.73(m,4H)、7.69~7.44(m、11H)、7.36~7.26(m,4H)、7.16~7.12(m,1H)、6.53~6.50(m,1H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.97 to 8.93 (m, 1 H), 8.87 to 8.83 (m, 1 H), 7.80 to 7.73 (m, 4 H) 7.69 to 7.44 (m, 11 H), 7.36 to 7.26 (m, 4 H), 7.16 to 7.12 (m, 1 H), 6.53 to 6.50 (m) , 1 H).
化合物(1-5):7-(10-フェニルアントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-5): 7- (10-phenylanthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.82~8.78(m,2H)、7.79~7.72(m,6H)、7.67~7.52(m,7H)、7.49~7.43(m,2H)、7.42(s,2H)、7.39~7.34(m,4H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.82 to 8.78 (m, 2 H), 7.79 to 7.72 (m, 6 H), 7.67 to 7.52 (m, 7 H) 7.49 to 7.43 (m, 2H), 7.42 (s, 2H), 7.39 to 7.34 (m, 4H).
化合物(1-121):3-(4-(10-フェニルアントラセン-9-イル)フェニル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-121): 3- (4- (10-phenylanthracene-9-yl) phenyl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.84~8.82(m,1H)、8.79~8.76(m,1H)、8.04~7.96(m,3H)、7.86~7.70(m,7H)、7.66~7.53(m,6H)、7.52~7.48(m,2H)、7.46~7.33(m,5H)、7.31~7.26(m,2H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.84 to 8.82 (m, 1 H), 8.79 to 8.76 (m, 1 H), 8.04 to 7.96 (m, 3 H) ), 7.86 to 7.70 (m, 7H), 7.66 to 7.53 (m, 6H), 7.52 to 7.48 (m, 2H), 7.46 to 7.33 (m) , 5H), 7.31 to 7.26 (m, 2H).
化合物(1-122):4-(4-(10-フェニルアントラセン-9-イル)フェニル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-122): 4- (4- (10-phenylanthracene-9-yl) phenyl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.82~8.78(m,2H)、8.00~7.90(m,5H)、7.85~7.80(m,1H)、7.77~7.72(m,3H)、7.67~7.51(m,9H)、7.47~7.35(m,5H)、7.29~7.23(m,2H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.82 to 8.78 (m, 2H), 8.00 to 7.90 (m, 5H), 7.85 to 7.80 (m, 1H) 7.77 to 7.72 (m, 3 H), 7.67 to 7.51 (m, 9 H), 7.47 to 7. 35 (m, 5 H), 7.29 to 7.23 (m) , 2H).
化合物(1-123):3-(3-(10-フェニルアントラセン-9-イル)フェニル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of compound (1-123): 3- (3- (10-phenylanthracene-9-yl) phenyl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.76~8.68(m,2H)、7.99~7.96(m,1H)、7.93~7.87(m,2H)、7.82~7.68(m,8H)、7.64~7.49(m,7H)、7.42~7.33(m,5H)、7.26~7.19(m,2H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.76 to 8.68 (m, 2 H), 7.99 to 7.96 (m, 1 H), 7.93 to 7.87 (m, 2 H) ), 7.82 to 7.68 (m, 8H), 7.64 to 7.49 (m, 7H), 7.42 to 7.33 (m, 5H), 7.26 to 7.19 (m) , 2H).
化合物(1-124):2-(4-(10-フェニルアントラセン-9-イル)フェニル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-124): 2- (4- (10-phenylanthracene-9-yl) phenyl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=9.08~9.05(m,1H)、8.87~8.83(m,1H)、8.14~8.10(m,1H)、8.00~7.96(m,2H)、7.87~7.81(m,3H)、7.78~7.70(m,4H)、7.67~7.53(m,6H)、7.53~7.44(m,3H)、7.41~7.33(m,4H)、7.31~7.26(m,2H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 9.08 to 9.05 (m, 1 H), 8.87 to 8.83 (m, 1 H), 8.14 to 8.10 (m, 1 H) 8.00 to 7.96 (m, 2 H), 7.87 to 7.8 1 (m, 3 H), 7.78 to 7. 70 (m, 4 H), 7.67 to 7.53 (m) , 6H), 7.53 to 7.44 (m, 3H), 7.41 to 7.33 (m, 4H), 7.31 to 7.26 (m, 2H).
化合物(1-221):3,11-ビス(10-フェニルアントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-221): 3,11-Bis (10-phenylanthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
MS(ACPI) m/z=775(M+H) The compound obtained by LC-MS measurement was confirmed to be the desired product.
MS (ACPI) m / z = 775 (M + H)
化合物(1-191):3-(9,9’-スピロビ[フルオレン]-2-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of compound (1-191): 3- (9,9'-spirobi [fluorene] -2-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.64~8.59(m,2H)、7.98~7.96(m,1H)、7.91~7.87(m,3H)、7.81~7.66(m,3H)、7.60~7.57(m,1H)、7.54~7.46(m,2H)、7.42~7.33(m,4H)、7.22~7.10(m,6H)、6.82~6.74(m,3H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.64 to 8.59 (m, 2H), 7.98 to 7.96 (m, 1H), 7.91 to 7.87 (m, 3H) ), 7.81 to 7.66 (m, 3H), 7.60 to 7.57 (m, 1H), 7.54 to 7.46 (m, 2H), 7.42 to 7.33 (m) , 4H), 7.22 to 7.10 (m, 6H), 6.82 to 6.74 (m, 3H).
化合物(1-198):3-(9,9’-スピロビ[フルオレン]-4-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of compound (1-198): 3- (9,9'-spirobi [fluorene] -4-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.90~8.85(m,1H)、8.82~8.79(m,1H)、7.88~7.81(m,4H)、7.78~7.73(m,1H)、7.68~7.64(m,1H)、7.62~7.58(m,1H)、7.47~7.37(m,3H)、7.32~7.26(m,3H)、7.20~7.13(m,4H)、7.06~6.98(m,2H)、6.87~6.81(m,2H)、6.79~6.75(m,1H)、6.73~6.69(m,1H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.90 to 8.85 (m, 1 H), 8.82 to 8.79 (m, 1 H), 7.88 to 7.81 (m, 4 H) 7.78 to 7.73 (m, 1 H), 7.68 to 7.64 (m, 1 H), 7.62 to 7.58 (m, 1 H), 7.47 to 7.37 (m) , 3H), 7.32 to 7.26 (m, 3H), 7.20 to 7.13 (m, 4H), 7.06 to 6.98 (m, 2H), 6.87 to 6.81 (M, 2H), 6.79 to 6.75 (m, 1 H), 6.73 to 6.69 (m, 1 H).
化合物(1-174):3-(ジベンゾ[g,p]クリセン-2-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-174): 3- (dibenzo [g, p] chrysene-2-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=9.11~9.08(m,1H)、8.88~8.72(m,9H)、8.06~8.02(m,2H)、7.91~7.81(m,2H)、7.77~7.65(m,7H)、7.60~7.57(m,1H)、7.46~7.41(m,1H)、7.32~7.24(m,2H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 9.11 to 9.08 (m, 1 H), 8.88 to 8.72 (m, 9 H), 8.06 to 8.02 (m, 2 H) 7.91 to 7.81 (m, 2H), 7.77 to 7.65 (m, 7H), 7.60 to 7.57 (m, 1 H), 7.46 to 7.41 (m) , 1 H), 7.32 to 7.24 (m, 2 H).
1H-NMR(400MHz,CDCl3):δ=9.3(s,1H)、8.9(d,1H)、8.8(dd,2H)、8.2(d,1H)、7.8(d,1H)、7.7(m,4H)、7.6(t,1H)、7.6~7.5(m,5H)、7.4(t,3H)、7.4(s,2H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 9.3 (s, 1 H), 8.9 (d, 1 H), 8.8 (dd, 2 H), 8.2 (d, 1 H), 7 7. 8 (d, 1 H), 7.7 (m, 4 H), 7.6 (t, 1 H), 7.6 to 7.5 (m, 5 H), 7.4 (t, 3 H), 7. 4 (s, 2 H).
1H-NMR(400MHz,CDCl3):δ=8.8(d,1H)、8.7(dd,1H)、8.3(s,1H)、8.2~8.1(m,2H)、8.1(s,1H)、8.0(dd,1H)、8.0(d,1H)、7.8(m,2H)、7.8~7.7(m,5H)、7.7~7.6(m,3H)、7.6(m,2H)、7.5(m,2H)、7.4(m,1H)、7.4~7.3(m,4H)、7.3(m,2H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.8 (d, 1 H), 8.7 (dd, 1 H), 8.3 (s, 1 H), 8.2 to 8.1 (m, 2H), 8.1 (s, 1 H), 8.0 (dd, 1 H), 8.0 (d, 1 H), 7.8 (m, 2 H), 7.8 to 7.7 (m, 5 H) ), 7.7 to 7.6 (m, 3 H), 7.6 (m, 2 H), 7.5 (m, 2 H), 7.4 (m, 1 H), 7.4 to 7.3 (c) m, 4H), 7.3 (m, 2H).
1H-NMR(400MHz,CDCl3):δ=8.9(m,1H)、8.8(m,1H)、8.4(s,1H)、8.2(d,1H)、8.1~8.0(m,4H)、7.9~7.8(m,2H)、7.8~7.5(m,11H)、7.5~7.4(m,1H)、7.4~7.3(m,4H)、7.3(m,3H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.9 (m, 1 H), 8.8 (m, 1 H), 8.4 (s, 1 H), 8.2 (d, 1 H), 8 1 to 8.0 (m, 4 H), 7.9 to 7.8 (m, 2 H), 7.8 to 7.5 (m, 11 H), 7.5 to 7.4 (m, 1 H) , 7.4 to 7.3 (m, 4H), 7.3 (m, 3H).
1H-NMR(400MHz,CDCl3):δ=8.7(dd,2H)、8.2(d,1H)、7.8~7.7(m,5H)、7.7~7.5(m,12H)、7.5(m,1H)、7.4(m,2H)、7.4~7.3(m,6H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.7 (dd, 2 H), 8.2 (d, 1 H), 7.8-7.7 (m, 5 H), 7.7-7. 5 (m, 12 H), 7.5 (m, 1 H), 7.4 (m, 2 H), 7.4 to 7.3 (m, 6 H).
化合物(1-82):2-(10-(2-ビフェニリル)アントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of compound (1-82): 2- (10- (2-biphenylyl) anthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.75~8.44(m,1H)、7.88~7.83(m,1H)、7.88~7.82(m,1H)、7.78~7.42(m,12H)、7.35~6.85(m,12H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.75 to 8.44 (m, 1 H), 7.88 to 7.83 (m, 1 H), 7.88 to 7.82 (m, 1 H) 7.78 to 7.42 (m, 12H), 7.35 to 6.85 (m, 12H).
化合物(1-52):2-(10-(1-ナフチル)アントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-52): 2- (10- (1-Naphthyl) anthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.90~8.80(m,1H)、8.58~8.49(m,1H)、8.11~8.00(m,2H)、7.93~7.80m,6H)、7.76~7.47(m,8H)、7.37~7.26(m,7H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.90 to 8.80 (m, 1 H), 8.58 to 8.49 (m, 1 H), 8.11 to 8.00 (m, 2 H) ), 7.93 to 7.80 m, 6H), 7.76 to 7.47 (m, 8 H), 7.37 to 7.26 (m, 7 H).
化合物(1-57):2-(10-(2-ナフチル)アントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of compound (1-57): 2- (10- (2-naphthyl) anthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.84~8.81(m,1H)、8.52~8.49(m,1H)、8.14~8.02(m,3H)、7.98~7.92(m,1H)、7.90~7.75(m,7H)、7.70~7.60(m,4H)、7.57~7.53(m,1H)、7.39~7.27(m,6H)、7.22~7.17(m,1H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.84 to 8.81 (m, 1 H), 8.52 to 8.49 (m, 1 H), 8.14 to 8.02 (m, 3 H) ), 7.98 to 7.92 (m, 1 H), 7.90 to 7.75 (m, 7 H), 7. 70 to 7. 60 (m, 4 H), 7.57 to 7.53 (m) , 1 H), 7.39 to 7.27 (m, 6 H), 7.22 to 7.17 (m, 1 H).
化合物(1-12):2-(9,10-ジフェニルアントラセン-2-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-12): 2- (9,10-Diphenylanthracene-2-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.88~8.85(m,1H)、8.56~8.53(m,1H)、8.08~8.06(m,1H)、7.94~7.90(m,1H)、7.88~7.84(m,1H)、7.82~7.71(m,5H)、7.70~7.52(m,12H)、7.43~7.32(m,3H)、7.26~7.22(m,2H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.88 to 8.85 (m, 1 H), 8.56 to 8.53 (m, 1 H), 8.08 to 8.06 (m, 1 H) 7.94 to 7.90 (m, 1 H), 7.88 to 7.84 (m, 1 H), 7.82 to 7.71 (m, 5 H), 7.70 to 7.52 (m) , 12H), 7.43 to 7.32 (m, 3H), 7.26 to 7.22 (m, 2H).
化合物(1-102):2-(10-(ジベンゾ[b,d]フラン-2-イル)アントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Compound (1-102): 2- (10- (dibenzo [b, d] furan-2-yl) anthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] Synthesis of anthracene
1H-NMR(400MHz,CDCl3):δ=8.83~8.80(m,1H)、8.51~8.48(m,1H)、8.13~8.09(m,1H)、7.96~7.93(m,1H)、7.90~7.74(m,8H)、7.70~7.60(m,3H)、7.57~7.50(m,2H)、7.41~7.28(m,7H)、7.22~7.16(m,1H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.83 to 8.80 (m, 1 H), 8.51 to 8.48 (m, 1 H), 8.13 to 8.09 (m, 1 H) 7.96-7.93 (m, 1 H), 7.90-7. 74 (m, 8 H), 7. 70-7. 60 (m, 3 H), 7.57-7. 50 (m) , 2H), 7.41 to 7.28 (m, 7H), 7.22 to 7.16 (m, 1 H).
化合物(1-182):2-(ブロモ-7,7-ジフェニル-7H-ベンゾ[c]フルオレン-5-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Compound (1-182): 2- (bromo-7,7-diphenyl-7H-benzo [c] fluoren-5-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene Synthesis of
1H-NMR(400MHz,CDCl3):δ=8.96~8.92(m,1H)、8.74~8.72(m,1H)、8.50~8.45(m,2H)、8.16~8.12(m,1H)、7.86~7.80(m,2H)、7.73~7.63(m,4H)、7.55~7.49(m,4H)、7.38~7.22(m,14H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.96 to 8.92 (m, 1 H), 8.74 to 8.72 (m, 1 H), 8.50 to 8.45 (m, 2 H) ), 8.16 to 8.12 (m, 1H), 7.86 to 7.80 (m, 2H), 7.73 to 7.63 (m, 4H), 7.55 to 7.49 (m) , 4H), 7.38 to 7.22 (m, 14H).
化合物(1-166):2-(ベンゾ[a]アントラセン-7-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-166): 2- (benzo [a] anthracene-7-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=9.34(s,1H)、8.96~8.93(m,1H)、8.74(s,1H)、8.47~8.43(m,1H)、8.25~8.22(m,1H)、7.89~7.71(m,6H)、7.66~7.43(m,7H)、7.35~7.27(m,2H)、7.17~7.12(m,1H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 9.34 (s, 1 H), 8.96 to 8.93 (m, 1 H), 8.74 (s, 1 H), 8.47 to 8. 43 (m, 1H), 8.25 to 8.22 (m, 1H), 7.89 to 7.71 (m, 6H), 7.66 to 7.43 (m, 7H), 7.35 to 7.27 (m, 2H), 7.17 to 7.12 (m, 1H).
化合物(1-55):7-(10-(1-ナフチル)アントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of Compound (1-55): 7- (10- (1-Naphthyl) anthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.81~8.77(m,2H)、8.10~8.00(m,2H)、7.82~7.70(m,5H)、7.63~7.57(m,3H)、7.53~7.43(m,7H)、7.35~7.19(m,6H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.81 to 8.77 (m, 2H), 8.10 to 8.00 (m, 2H), 7.82 to 7.70 (m, 5H) ), 7.63 to 7.57 (m, 3H), 7.53 to 7.43 (m, 7H), 7.35 to 7.19 (m, 6H).
化合物(1-85):2-(10-(2-ビフェニリル)アントラセン-9-イル)-5,9-ジオキサ-13b-ボラナフト[3,2,1-de]アントラセンの合成
Synthesis of compound (1-85): 2- (10- (2-biphenylyl) anthracene-9-yl) -5,9-dioxa-13b-boranaphtho [3,2,1-de] anthracene
1H-NMR(400MHz,CDCl3):δ=8.79~8.75(m,2H)、7.76~7.63(m,8H)、7.60~7.53(m,3H)、7.50~7.41(m,3H)、7.37~7.35(m,1H)、7.32~7.23(m,5H)、7.02~6.99(m,2H)、6.95~6.87(m,3H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.79 to 8.75 (m, 2 H), 7.76 to 7.63 (m, 8 H), 7.60 to 7.53 (m, 3 H) ), 7.50 to 7.41 (m, 3H), 7.37 to 7.35 (m, 1 H), 7.32 to 7.23 (m, 5 H), 7.02 to 6.99 (m) , 2H), 6.95 to 6.87 (m, 3H).
化合物(1-46):9-(10-フェニルアントラセン-9-イル)-7,11-ジオキサ-17c-ボラナフト[2,3,4-no]テトラフェンの合成
Synthesis of Compound (1-46): 9- (10-phenylanthracene-9-yl) -7,11-dioxa-17c-boranaphtho [2,3,4-no] tetraphen
1H-NMR(400MHz,CDCl3):δ=8.21~8.17(m,2H)、7.96~7.92(m,2H)、7.87~7.83(m,2H)、7.78~7.71(m,6H)、7.65~7.43(m,9H)、7.37~7.30(m,4H)、7.17~7.12(m,2H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.21 to 8.17 (m, 2H), 7.96 to 7.92 (m, 2H), 7.87 to 7.83 (m, 2H) 7.78 to 7.71 (m, 6 H), 7.65 to 7.43 (m, 9 H), 7.37 to 7.30 (m, 4 H), 7.17 to 7.12 (m) , 2H).
比較例用化合物(EM-3)の合成
1H-NMR(400MHz,1,1,2,2-tetrachloroethane-d2、80oC):δ=7.3~7.4(m,4H)、7.5(dd,4H)、7.6(s,4H)、7.7(m,4H)、8.6(dd,4H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, 1,1,2,2-tetrachloroethane-d2, 80 ° C.): δ = 7.3 to 7.4 (m, 4H), 7.5 (dd, 4H), 7. 6 (s, 4 H), 7.7 (m, 4 H), 8.6 (dd, 4 H).
1H-NMR:δ=8.92(s,1H)、8.86(s,1H)、7.68(s,1H)、7.67(d,2H)、7.64(d,1H)、7.48(dd,1H)、7.43(dd,1H)、7.27~7.14(m,5H)、7.00~6.98(m,3H)、6.71(d,1H)、6.65(d,1H)、6.05(s,1H)、5.90(s,1H)、2.17(s,3H)、1.48(s,9H)、1.46(s,9H)、1.45(s,9H)、1.43(s,9H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR: δ = 8.92 (s, 1 H), 8.86 (s, 1 H), 7.68 (s, 1 H), 7.67 (d, 2 H), 7.64 (d, 1 H) ), 7.48 (dd, 1 H), 7.43 (dd, 1 H), 7.27 to 7.14 (m, 5 H), 7.00 to 6.98 (m, 3 H), 6.71 (m, 3 H) d, 1 H), 6.65 (d, 1 H), 6.05 (s, 1 H), 5. 90 (s, 1 H), 2.17 (s, 3 H), 1.48 (s, 9 H), 1.46 (s, 9 H), 1. 45 (s, 9 H), 1.43 (s, 9 H).
1H-NMR:δ=1.4(s,9H)、1.4(s,9H)、1.5(s,9H)、1.5(s,9H)、1.9(s,6H)、6.1(d,1H)、6.2(d,1H)、6.6(s,1H)、6.7(d,1H)、6.8(d,1H)、7.2~7.3(m,6H)、7.5(m,2H)、7.6(m,1H)、7.6~7.7(m,3H)、8.9(d,1H)、8.9(d,1H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR: δ = 1.4 (s, 9 H), 1.4 (s, 9 H), 1.5 (s, 9 H), 1.5 (s, 9 H), 1.9 (s, 6 H) ), 6.1 (d, 1 H), 6.2 (d, 1 H), 6.6 (s, 1 H), 6.7 (d, 1 H), 6.8 (d, 1 H), 7.2. To 7.3 (m, 6 H), 7.5 (m, 2 H), 7.6 (m, 1 H), 7.6 to 7.7 (m, 3 H), 8.9 (d, 1 H), 8.9 (d, 1 H).
1H-NMR:δ=1.1(s,9H)、1.4(s,9H)、1.5(s,9H)、1.5(s,9H)、1.5(s,9H)、6.1(d,1H)、6.2(d,1H)、6.7(d,1H)、6.8(d,1H)、7.0(d,1H)、7.1(d,1H)、7.2~7.3(m,7H)、7.5(dd,1H)、7.5(dd,1H)、7.7(m,3H)、8.9(d,1H)、8.9(d,1H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR: δ = 1.1 (s, 9 H), 1.4 (s, 9 H), 1.5 (s, 9 H), 1.5 (s, 9 H), 1.5 (s, 9 H) ), 6.1 (d, 1 H), 6.2 (d, 1 H), 6.7 (d, 1 H), 6.8 (d, 1 H), 7.0 (d, 1 H), 7.1 (D, 1 H), 7.2 to 7.3 (m, 7 H), 7.5 (dd, 1 H), 7.5 (dd, 1 H), 7.7 (m, 3 H), 8.9 (c) d, 1 H), 8.9 (d, 1 H).
1H-NMR:δ=1.1(s,9H)、1.4(s,9H)、1.5(s,9H)、1.5(s,9H)、1.5(s,9H)、2.2(s,3H)、5.9(s,1H)、6.1(s,1H)、6.7(m,2H)、7.0(d,2H)、7.1(d,2H)、7.2(d,1H)、7.3(m,2H)、7.4(m,1H)、7.5(m,1H)、7.6(dd,1H)、7.7(m,3H)、8.9(d,1H)、8.9(d,1H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR: δ = 1.1 (s, 9 H), 1.4 (s, 9 H), 1.5 (s, 9 H), 1.5 (s, 9 H), 1.5 (s, 9 H) ), 2.2 (s, 3 H), 5.9 (s, 1 H), 6.1 (s, 1 H), 6.7 (m, 2 H), 7.0 (d, 2 H), 7.1 (D, 2 H), 7.2 (d, 1 H), 7.3 (m, 2 H), 7.4 (m, 1 H), 7.5 (m, 1 H), 7.6 (dd, 1 H) 7.7 (m, 3 H), 8.9 (d, 1 H), 8.9 (d, 1 H).
1H-NMR:δ=1.0(s,18H)、1.5(s,9H)、1.6(s,9H)、1.6(s,9H)、1.6(s,9H)、6.2(d,1H)、6.4(d,1H)、6.8(d,1H)、6.9(d,2H)、7.0(d,1H)、7.0(m,1H)、7.3~7.4(m,3H)、7.5(d,1H)、7.6(dd,1H)、7.6(m,1H)、7.8(m,4H)、8.9(d,1H)、9.0(d,1H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR: δ = 1.0 (s, 18 H), 1.5 (s, 9 H), 1.6 (s, 9 H), 1.6 (s, 9 H), 1.6 (s, 9 H) ), 6.2 (d, 1 H), 6.4 (d, 1 H), 6.8 (d, 1 H), 6.9 (d, 2 H), 7.0 (d, 1 H), 7.0 (M, 1 H), 7.3 to 7.4 (m, 3 H), 7.5 (d, 1 H), 7.6 (dd, 1 H), 7.6 (m, 1 H), 7.8 (m, 1 H) m, 4H), 8.9 (d, 1 H), 9.0 (d, 1 H).
1H-NMR:δ=1.0(s,9H)、1.4(s,9H)、1.5(s,18H)、1.5(s,9H)、6.0(s,1H)、6.1(s,1H)、6.7(d,1H)、6.9(d,1H)、7.0(m,3H)、7.1~7.2(m,2H)、7.3(m,3H)、7.5(m,2H)、7.6~7.7(m,4H)、8.9(d,1H)、8.9(d,1H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR: δ = 1.0 (s, 9 H), 1.4 (s, 9 H), 1.5 (s, 18 H), 1.5 (s, 9 H), 6.0 (s, 1 H) ), 6.1 (s, 1 H), 6.7 (d, 1 H), 6.9 (d, 1 H), 7.0 (m, 3 H), 7.1 to 7.2 (m, 2 H) , 7.3 (m, 3 H), 7.5 (m, 2 H), 7.6 to 7.7 (m, 4 H), 8.9 (d, 1 H), 8.9 (d, 1 H).
1H-NMR(400MHz,CDCl3):δ=8.93(s,1H)、8.89(s,1H)、7.68~7.61(m,4H)、7.50~7.47(m,2H)、7.28~7.22(m,4H)、7.16(d,2H)、6.99~6.98(m,3H)、6.78(d,1H)、6.71(d,1H)、6.22(d,1H)、6.07(d,1H)、1.48(s,9H)、1.45(s,18H)、1.44(s,9H). The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (400 MHz, CDCl 3 ): δ = 8.93 (s, 1 H), 8.89 (s, 1 H), 7.68-7.61 (m, 4 H), 7.50-7. 47 (m, 2H), 7.28 to 7.22 (m, 4H), 7.16 (d, 2H), 6.99 to 6.98 (m, 3H), 6.78 (d, 1H) , 6.71 (d, 1 H), 6.22 (d, 1 H), 6.07 (d, 1 H), 1.48 (s, 9 H), 1.45 (s, 18 H), 1.44 ( s, 9H).
1H-NMR(500MHz,CDCl3):δ=1.47(s,36H)、2.17(s,3H)、5.97(s,2H)、6.68(d,2H)、7.28(d,4H、7.49(dd,2H)、7.67(d,4H)、8.97(d,2H). Compound (1-2619) was synthesized using the same method as the above-mentioned synthesis example. The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (500 MHz, CDCl 3 ): δ = 1.47 (s, 36 H), 2.17 (s, 3 H), 5.97 (s, 2 H), 6.68 (d, 2 H), 7 28 (d, 4H, 7.49 (dd, 2H), 7.67 (d, 4H), 8.97 (d, 2H).
1H-NMR(500MHz,CDCl3):δ=8.98~8.96(m,2H)、7.70~7.65(m,4H)、7.51~7.47(m,2H)、7.31~7.26(m,4H)、6.78~6.75(m,2H)、6.11(s,2H)、1.47~1.44(m,18H)、0.93(s,9H). Compound (2-2710) was synthesized using the same method as the above-mentioned synthesis example. The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (500 MHz, CDCl 3 ): δ = 8.98 to 8.96 (m, 2H), 7.70 to 7.65 (m, 4H), 7.51 to 7.47 (m, 2H) ), 7.31 to 7.26 (m, 4H), 6.78 to 6.75 (m, 2H), 6.11 (s, 2H), 1.47 to 1.44 (m, 18H), 0.93 (s, 9H).
1H-NMR(500MHz,CDCl3):δ=9.20~8.60(m,2H)、7.65~7.20(m,8H)、7.20~7.05(m,7H)、6.85~6.50(m,10H)、6.20~5.20(m,2H)、1.46~1.44(m,36H). Compound (2-2711) was synthesized using the same method as the synthesis example described above. The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (500 MHz, CDCl 3 ): δ = 9.20 to 8.60 (m, 2H), 7.65 to 7.20 (m, 8H), 7.20 to 7.05 (m, 7H) 6.85 to 6.50 (m, 10H), 6.20 to 5.20 (m, 2H), 1.46 to 1.44 (m, 36H).
1H-NMR(500MHz,CDCl3):δ=9.00~8.95(m,2H)、7.48~7.36(m,6H)、7.20~6.95(m,10H)、6.90~6.52(m,12H)、6.48~6.26(m,2H)、5.60~5.00(m,2H)、1.46(s,18H)、1.26(s,18H). The compound (2-2712) was synthesized using the same method as the synthesis example described above. The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (500 MHz, CDCl 3 ): δ = 9.00 to 8.95 (m, 2 H), 7.48 to 7.36 (m, 6 H), 7.20 to 6.95 (m, 10 H) 6.90 to 6.52 (m, 12 H), 6.48 to 6.26 (m, 2 H), 5. 60 to 5.00 (m, 2 H), 1.46 (s, 18 H), 1.26 (s, 18H).
1H-NMR(500MHz,CDCl3):δ=8.95~8.88(m,2H)、7.71~7.64(m,3H)、7.61~7.56(m,1H)、7.50~7.43(m,2H)、7.28~7.20(m,3H)、7.11~7.07(m,2H)、7.01~6.97(m,2H)、6.85~6.80(m,1H)、6.76~6.72(m,1H)、6.16(s,1H)、6.05(s,1H)、1.48~1.43(m,27H)、1.11(s,9H)、0.97(s,9H). The compound (2-301) was synthesized using the same method as the synthesis example described above. The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (500 MHz, CDCl 3 ): δ = 8.95 to 8.88 (m, 2H), 7.71 to 7.64 (m, 3H), 7.61 to 7.56 (m, 1H) ), 7.50 to 7.43 (m, 2H), 7.28 to 7.20 (m, 3H), 7.11 to 7.07 (m, 2H), 7.01 to 6.97 (m) , 2H), 6.85 to 6.80 (m, 1 H), 6.76 to 6.72 (m, 1 H), 6.16 (s, 1 H), 6.05 (s, 1 H), 48 to 1.43 (m, 27 H), 1. 11 (s, 9 H), 0.97 (s, 9 H).
1H-NMR(500MHz,CDCl3):δ=8.90~8.87(m,1H)、8.75~8.72(m,1H)、7.73~7.58(m,4H)、7.48~7.43(m,1H)、7.35~7.19(m,5H)、7.11~7.07(d,2H)、7.01~6.97(d,2H)、6.67~6.64(m,2H)、6.17(s,1H)、5.94(s,1H)、1.50~1.43(m,27H)、1.18(s,9H)、1.11(s,9H). Compound (2-302) was synthesized using the same method as the above-mentioned synthesis example. The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (500 MHz, CDCl 3 ): δ = 8.90 to 8.87 (m, 1 H), 8.75 to 8.72 (m, 1 H), 7.73 to 7.58 (m, 4 H) ), 7.48 to 7.43 (m, 1 H), 7. 35 to 7. 19 (m, 5 H), 7.1 1 to 7.0 7 (d, 2 H), 7.0 1 to 6. 97 (d) , 2H), 6.67 to 6.64 (m, 2H), 6.17 (s, 1 H), 5.94 (s, 1 H), 1.50 to 1.43 (m, 27 H), 18 (s, 9 H), 1. 11 (s, 9 H).
1H-NMR(500MHz,CDCl3):δ=8.96~8.95(m,2H)、7.47~7.42(m,6H)、7.15~7.10(m,4H)、6.77~6.74(m,2H)、5.56(s,2H)、1.46(m,9H)、1.33(s,9H). Compound (2-2714) was synthesized using the same method as the above-mentioned synthesis example. In the chemical formulae, D is deuterium. The structure of the obtained compound was confirmed by NMR measurement.
1 H-NMR (500 MHz, CDCl 3 ): δ = 8.96 to 8.95 (m, 2H), 7.47 to 7.42 (m, 6H), 7.15 to 7.10 (m, 4H) 6.77 to 6.74 (m, 2H), 5.56 (s, 2H), 1.46 (m, 9H), 1.33 (s, 9H).
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置(昭和真空(株)製)の基板ホルダーに固定し、HI、IL、HT-1、HT-2、化合物(1-1)、化合物(2-2619)、ET-1およびET-2をそれぞれ入れたモリブデン製蒸着用ボート、Liq、マグネシウムおよび銀をそれぞれ入れた窒化アルミニウム製蒸着用ボートを装着した。 Example A-1
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) was used as a transparent support substrate, in which ITO formed to a thickness of 180 nm by sputtering was polished to 150 nm. The transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and HI, IL, HT-1, HT-2, compound (1-1), compound (2-2619), A molybdenum deposition boat containing ET-1 and ET-2, respectively, and an aluminum nitride deposition boat containing Liq and magnesium and silver, respectively, were mounted.
ホスト材料及びドーパント材料を上記表に記載した材料に変更した以外は実施例A-1に準じて有機EL素子を作製し、同様にして有機EL特性を測定した。 Comparative Examples A-1 and A-2
An organic EL device was produced according to Example A-1 except that the host material and the dopant material were changed to the materials listed in the above table, and the organic EL characteristics were similarly measured.
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置(昭和真空(株)製)の基板ホルダーに固定し、HI、IL、HT-1、HT-2、化合物(1-1)、化合物(2-2619)、ET-1およびET-2をそれぞれ入れたタンタル製蒸着用ボート、Liq、LiFおよびアルミニウムをそれぞれ入れた窒化アルミニウム製蒸着用ボートを装着した。 Example B-1
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) was used as a transparent support substrate, in which ITO formed to a thickness of 180 nm by sputtering was polished to 150 nm. The transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and HI, IL, HT-1, HT-2, compound (1-1), compound (2-2619), A tantalum deposition boat containing ET-1 and ET-2, respectively, and an aluminum nitride deposition boat containing Liq, LiF and aluminum, respectively, were mounted.
ホスト材料及びドーパント材料を上記表に記載した材料に変更した以外は実施例B-1に準じて有機EL素子を作製し、同様にして有機EL特性を測定した。 Examples B-2 to B-15 and Comparative Examples B-1 to B-2
An organic EL device was produced according to Example B-1 except that the host material and the dopant material were changed to the materials listed in the above table, and the organic EL characteristics were similarly measured.
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置(長州産業(株)製)の基板ホルダーに固定し、HI、IL、HT-1、HT-2、化合物(1-82)、化合物(2-2619)、ET-1およびET-2をそれぞれ入れたタンタル製蒸着用ボート、Liq、LiFおよびアルミニウムをそれぞれ入れた窒化アルミニウム製蒸着用ボートを装着した。 Example B-16
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) was used as a transparent support substrate, in which ITO formed to a thickness of 180 nm by sputtering was polished to 150 nm. The transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (made by Choshu Sangyo Co., Ltd.), and HI, IL, HT-1, HT-2, compound (1-82), compound (2-2619), A tantalum deposition boat containing ET-1 and ET-2, respectively, and an aluminum nitride deposition boat containing Liq, LiF and aluminum, respectively, were mounted.
ホスト材料及びドーパント材料を上記表に記載した材料に変更した以外は実施例B-16に準じて有機EL素子を作製し、同様にして有機EL特性を測定した。 Examples B-17 to B-23 and Comparative Example B-3
An organic EL device was produced according to Example B-16 except that the host material and the dopant material were changed to the materials listed in the above table, and the organic EL characteristics were similarly measured.
スパッタリングにより180nmの厚さに製膜したITOを150nmまで研磨した、26mm×28mm×0.7mmのガラス基板((株)オプトサイエンス製)を透明支持基板とした。この透明支持基板を市販の蒸着装置(昭和真空(株)製)の基板ホルダーに固定し、HI、IL、HT-1、HT-2、化合物(1-2)、化合物(2-166)、ET-1およびET-2をそれぞれ入れたタンタル製蒸着用ボート、Liq、LiFおよびアルミニウムをそれぞれ入れた窒化アルミニウム製蒸着用ボートを装着した。 Example C-1
A 26 mm × 28 mm × 0.7 mm glass substrate (manufactured by Opto Science Co., Ltd.) was used as a transparent support substrate, in which ITO formed to a thickness of 180 nm by sputtering was polished to 150 nm. The transparent support substrate is fixed to a substrate holder of a commercially available vapor deposition apparatus (manufactured by Showa Vacuum Co., Ltd.), and HI, IL, HT-1, HT-2, compound (1-2), compound (2-166), A tantalum deposition boat containing ET-1 and ET-2, respectively, and an aluminum nitride deposition boat containing Liq, LiF and aluminum, respectively, were mounted.
ホスト材料及びドーパント材料を上記表に記載した材料に変更した以外は実施例C-1に準じて有機EL素子を作製し、同様にして有機EL特性を測定した。 Examples C-2 to C-14
An organic EL device was produced according to Example C-1 except that the host material and the dopant material were changed to the materials listed in the above table, and the organic EL characteristics were similarly measured.
101 基板
102 陽極
103 正孔注入層
104 正孔輸送層
105 発光層
106 電子輸送層
107 電子注入層
108 陰極 100 organic electroluminescent device 101
Claims (13)
- 下記一般式(1)で表される多環芳香族化合物。
X1およびX2は、それぞれ独立して、>O、>Sまたは>Seであり、
R1、R2、R3、R4、R5、R6、R7、R8、R9、R10およびR11は、それぞれ独立して、水素、アルキル、またはアルキルで置換されていてもよいアリールであり、R1~R11のうちの隣接する基同士が結合してa環、b環またはc環と共にアリール環を形成していてもよく、形成されたアリール環における少なくとも1つの水素はアルキルで置換されていてもよく、
R1~R11のうちの少なくとも1つは、それぞれ独立して、下記式(Z-1)、式(Z-2)、式(Z-3)、式(Z-4)、式(Z-5)または式(Z-6)で表される基であり、
上記式(Z-1)~式(Z-6)中のArは、それぞれ独立して、下記式(Ar-1)、式(Ar-2)、式(Ar-3)、式(Ar-4)、式(Ar-5)、式(Ar-6)、式(Ar-7)、式(Ar-8)、式(Ar-9)、式(Ar-10)、式(Ar-11)または式(Ar-12)で表される基であり、
上記式(Ar-1)~式(Ar-12)中、Xは、それぞれ独立して、水素、炭素数1~4のアルキル、炭素数1~4のアルキルで置換されていてもよい炭素数6~18のアリール、または炭素数1~4のアルキルで置換されていてもよい炭素数2~18のヘテロアリールであり、A1とA2は、共に、水素であるか、または互いに結合してスピロ環を形成してもよく、式(Ar-1)および式(Ar-2)中の「-Xn」は、n個のXがそれぞれ独立して任意の位置に結合することを示し、nは1~4の整数であり、
上記式(1)で表される化合物における少なくとも1つの水素は重水素で置換されていてもよい。) The polycyclic aromatic compound represented by following General formula (1).
X 1 and X 2 are each independently>O,> S or> Se,
R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , R 8 , R 9 , R 10 and R 11 are each independently substituted with hydrogen, alkyl or alkyl And adjacent groups of R 1 to R 11 may combine to form an aryl ring together with the a ring, b ring or c ring, and at least one of the formed aryl rings is Hydrogen may be substituted by alkyl,
At least one of R 1 to R 11 is each independently represented by the following formula (Z-1), formula (Z-2), formula (Z-3), formula (Z-4), or formula (Z) -5) or a group represented by formula (Z-6),
Ar in each of the above formulas (Z-1) to (Z-6) is independently at each of the following formulas (Ar-1), (Ar-2), (Ar-3), and (Ar-). 4) Formula (Ar-5), Formula (Ar-6), Formula (Ar-7), Formula (Ar-8), Formula (Ar-9), Formula (Ar-10), Formula (Ar-11) Or a group represented by formula (Ar-12),
In the above formulas (Ar-1) to (Ar-12), X is each independently hydrogen, alkyl having 1 to 4 carbon atoms, or carbon number which may be substituted with alkyl having 1 to 4 carbon atoms 6 to 18 aryl or C 2 to C 18 heteroaryl which may be substituted with C 1 to C 4 alkyl, and A 1 and A 2 are both hydrogen or they are bonded to each other May form a spiro ring, and “—Xn” in the formula (Ar-1) and the formula (Ar-2) indicates that n Xs independently bind to any position, n is an integer of 1 to 4 and
At least one hydrogen in the compound represented by the above formula (1) may be substituted with deuterium. ) - 上記式(1)中、
X1およびX2は、それぞれ独立して、>O、>Sまたは>Seであり、
R1~R11は、それぞれ独立して、水素、炭素数1~12のアルキル、または炭素数1~12のアルキルで置換されていてもよい炭素数6~24のアリールであり、R1~R11のうちの隣接する基同士が結合してa環、b環またはc環と共に炭素数10~20のアリール環を形成していてもよく、形成されたアリール環における少なくとも1つの水素は炭素数1~12のアルキルで置換されていてもよく、
R1~R11のうちの1つまたは2つは、それぞれ独立して、上記式(Z-1)、式(Z-2)、式(Z-3)、式(Z-4)、式(Z-5)または式(Z-6)で表される基であり、
上記式(Z-1)~式(Z-6)中のArは、それぞれ独立して、上記式(Ar-1)、式(Ar-2)、式(Ar-3)、式(Ar-4)、式(Ar-5)、式(Ar-6)、式(Ar-7)、式(Ar-8)、式(Ar-9)、式(Ar-10)、式(Ar-11)または式(Ar-12)で表される基であり、
上記式(Ar-1)~式(Ar-12)中、Xは、それぞれ独立して、水素、炭素数1~4のアルキル、炭素数1~4のアルキルで置換されていてもよい炭素数6~18のアリール、または炭素数1~4のアルキルで置換されていてもよい炭素数4~16のヘテロアリールであり、A1とA2は、共に、水素であるか、または互いに結合してスピロ環を形成してもよく、式(Ar-1)および式(Ar-2)中の「-Xn」は、n個のXがそれぞれ独立して任意の位置に結合することを示し、nは1~4の整数であり、
上記式(1)で表される化合物における少なくとも1つの水素は重水素で置換されていてもよい、
請求項1に記載する、多環芳香族化合物。 In the above formula (1),
X 1 and X 2 are each independently>O,> S or> Se,
R 1 to R 11 are each independently hydrogen, alkyl having 1 to 12 carbons, or aryl having 6 to 24 carbons which may be substituted with alkyl having 1 to 12 carbons, and R 1 to Adjacent groups of R 11 may combine to form an aryl ring having a carbon number of 10 to 20 together with the a ring, b ring or c ring, and at least one hydrogen in the formed aryl ring is carbon It may be substituted by the alkyl of the number 1-12,
One or two of R 1 to R 11 are each independently the above-mentioned formula (Z-1), formula (Z-2), formula (Z-3), formula (Z-4), formula A group represented by (Z-5) or formula (Z-6),
Ar in the above formulas (Z-1) to (Z-6) is independently at least one of the above formulas (Ar-1), (Ar-2), (Ar-3), and (Ar-). 4) Formula (Ar-5), Formula (Ar-6), Formula (Ar-7), Formula (Ar-8), Formula (Ar-9), Formula (Ar-10), Formula (Ar-11) Or a group represented by formula (Ar-12),
In the above formulas (Ar-1) to (Ar-12), X is each independently hydrogen, alkyl having 1 to 4 carbon atoms, or carbon number which may be substituted with alkyl having 1 to 4 carbon atoms 6 to 18 aryl or C 4 to C 16 heteroaryl optionally substituted with alkyl having 1 to 4 carbon atoms, and A 1 and A 2 are both hydrogen or are bonded to each other May form a spiro ring, and “—Xn” in the formula (Ar-1) and the formula (Ar-2) indicates that n Xs independently bind to any position, n is an integer of 1 to 4 and
At least one hydrogen in the compound represented by the above formula (1) may be substituted with deuterium.
The polycyclic aromatic compound according to claim 1. - 上記式(1)中、
X1およびX2は、>Oであり、
R1~R11は、それぞれ独立して、水素、炭素数1~6のアルキル、または炭素数1~6のアルキルで置換されていてもよい炭素数6~18のアリールであり、R1~R11のうちの隣接する基同士が結合してa環、b環またはc環と共に炭素数10~18のアリール環を形成していてもよく、形成されたアリール環における少なくとも1つの水素は炭素数1~6のアルキルで置換されていてもよく、
R1~R11のうちの1つまたは2つは、それぞれ独立して、上記式(Z-1)、式(Z-2)、式(Z-3)、式(Z-4)、式(Z-5)または式(Z-6)で表される基であり、
上記式(Z-1)~式(Z-6)中のArは、それぞれ独立して、下記式(Ar-1-1)、式(Ar-1-2)、式(Ar-2-1)、式(Ar-2-2)、式(Ar-2-3)、式(Ar-3)、式(Ar-4-1)、式(Ar-5-1)、式(Ar-5-2)、式(Ar-5-3)、式(Ar-6)、式(Ar-7)、式(Ar-8)、式(Ar-9)、式(Ar-10)、式(Ar-11)または式(Ar-12)で表される基であり、
請求項1に記載する、多環芳香族化合物。 In the above formula (1),
X 1 and X 2 are> O,
R 1 - R 11 are each independently hydrogen, alkyl having 1 to 6 carbon atoms or an alkyl aryl of 6-18 carbon atoms which may be substituted having 1 to 6 carbon atoms,, R 1 - Adjacent groups of R 11 may combine to form an aryl ring having a carbon number of 10 to 18 together with the a ring, b ring or c ring, and at least one hydrogen in the formed aryl ring is carbon It may be substituted with alkyl of 1 to 6,
One or two of R 1 to R 11 are each independently the above-mentioned formula (Z-1), formula (Z-2), formula (Z-3), formula (Z-4), formula A group represented by (Z-5) or formula (Z-6),
Ar in the above formulas (Z-1) to (Z-6) is independently at least one of the following formulas (Ar-1-1), (Ar-1-2), and (Ar-2-1). ), Formula (Ar-2-2), formula (Ar-2-3), formula (Ar-3), formula (Ar-4-1), formula (Ar-5-1), formula (Ar-5) -2), formula (Ar-5-3), formula (Ar-6), formula (Ar-7), formula (Ar-8), formula (Ar-9), formula (Ar-10), formula ( Ar-11) or a group represented by formula (Ar-12),
The polycyclic aromatic compound according to claim 1. - 請求項1~4のいずれかに記載する多環芳香族化合物を含有する、有機デバイス用材料。 A material for an organic device comprising the polycyclic aromatic compound according to any one of claims 1 to 4.
- 前記有機デバイス用材料が、有機電界発光素子用材料、有機電界効果トランジスタ用材料または有機薄膜太陽電池用材料である、請求項5に記載する有機デバイス用材料。 The material for an organic device according to claim 5, wherein the material for an organic device is a material for an organic electroluminescent device, a material for an organic field effect transistor, or a material for an organic thin film solar cell.
- 発光層用材料である、請求項6に記載する有機電界発光素子用材料。 The material for an organic electroluminescent element according to claim 6, which is a material for a light emitting layer.
- さらに、下記一般式(2)で表される多環芳香族化合物および下記一般式(2)で表される構造を複数有する多環芳香族化合物の多量体の少なくとも1つを含有する、請求項7に記載する発光層用材料。
A環、B環およびC環は、それぞれ独立して、アリール環またはヘテロアリール環であり、これらの環における少なくとも1つの水素は置換されていてもよく、
X1およびX2はそれぞれ独立して>Oまたは>N-Rであり、前記>N-RのRは置換されていてもよいアリール、置換されていてもよいヘテロアリールまたはアルキルであり、また、前記N-RのRは連結基または単結合により前記A環、B環および/またはC環と結合していてもよく、そして、
式(2)で表される化合物または構造における少なくとも1つの水素がハロゲン、シアノまたは重水素で置換されていてもよい。) Furthermore, it contains at least one of a polycyclic aromatic compound represented by the following general formula (2) and a polymer of a polycyclic aromatic compound having a plurality of structures represented by the following general formula (2). The light emitting layer material described in 7.
Ring A, ring B and ring C are each independently an aryl ring or a heteroaryl ring, and at least one hydrogen in these rings may be substituted.
X 1 and X 2 are each independently> O or> N—R, and R in the aforementioned> N—R is optionally substituted aryl, optionally substituted heteroaryl or alkyl, and And R in said NR may be bonded to said A ring, B ring and / or C ring by a linking group or a single bond, and
At least one hydrogen in the compound or structure represented by Formula (2) may be substituted with halogen, cyano or deuterium. ) - 陽極および陰極からなる一対の電極と、該一対の電極間に配置され、請求項7または8に記載する発光層用材料を含有する発光層とを有する、有機電界発光素子。 An organic electroluminescent device comprising: a pair of electrodes comprising an anode and a cathode; and a light emitting layer disposed between the pair of electrodes and containing the material for a light emitting layer according to claim 7 or 8.
- さらに、前記陰極と該発光層との間に配置される電子輸送層および/または電子注入層を有し、該電子輸送層および電子注入層の少なくとも1つは、ボラン誘導体、ピリジン誘導体、フルオランテン誘導体、BO系誘導体、アントラセン誘導体、ベンゾフルオレン誘導体、ホスフィンオキサイド誘導体、ピリミジン誘導体、カルバゾール誘導体、トリアジン誘導体、ベンゾイミダゾール誘導体、フェナントロリン誘導体、およびキノリノール系金属錯体からなる群から選択される少なくとも1つを含有する、請求項9に記載する有機電界発光素子。 Furthermore, it has an electron transport layer and / or an electron injection layer disposed between the cathode and the light emitting layer, and at least one of the electron transport layer and the electron injection layer is a borane derivative, a pyridine derivative, a fluoranthene derivative , At least one selected from the group consisting of BO derivatives, anthracene derivatives, benzofluorene derivatives, phosphine oxide derivatives, pyrimidine derivatives, carbazole derivatives, triazine derivatives, benzimidazole derivatives, phenanthroline derivatives, and quinolinol metal complexes An organic electroluminescent device according to claim 9.
- 前記電子輸送層および/または電子注入層が、さらに、アルカリ金属、アルカリ土類金属、希土類金属、アルカリ金属の酸化物、アルカリ金属のハロゲン化物、アルカリ土類金属の酸化物、アルカリ土類金属のハロゲン化物、希土類金属の酸化物、希土類金属のハロゲン化物、アルカリ金属の有機錯体、アルカリ土類金属の有機錯体および希土類金属の有機錯体からなる群から選択される少なくとも1つを含有する、請求項10に記載の有機電界発光素子。 The electron transport layer and / or the electron injection layer may further be selected from alkali metals, alkaline earth metals, rare earth metals, oxides of alkali metals, halides of alkali metals, oxides of alkaline earth metals, and alkaline earth metals. The at least one selected from the group consisting of halides, oxides of rare earth metals, halides of rare earth metals, organic complexes of alkali metals, organic complexes of alkaline earth metals, and organic complexes of rare earth metals. The organic electroluminescent element as described in 10.
- 請求項9~11のいずれかに記載する有機電界発光素子を備えた表示装置。 A display comprising the organic electroluminescent device according to any one of claims 9 to 11.
- 請求項9~11のいずれかに記載する有機電界発光素子を備えた照明装置。 A lighting device comprising the organic electroluminescent device according to any one of claims 9 to 11.
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US20210167288A1 (en) | 2021-06-03 |
CN110719914B (en) | 2023-07-28 |
JPWO2019009052A1 (en) | 2020-04-30 |
JP2022188012A (en) | 2022-12-20 |
KR102561085B1 (en) | 2023-07-27 |
TWI773785B (en) | 2022-08-11 |
JP7148932B2 (en) | 2022-10-06 |
US11600790B2 (en) | 2023-03-07 |
TW201906851A (en) | 2019-02-16 |
CN110719914A (en) | 2020-01-21 |
KR20200026182A (en) | 2020-03-10 |
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